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Iron (III) Chloride as an Efficient Catalyst for Stereoselective
Synthesis of Glycosyl Azides and a Cocatalyst with Cu(0) for the
Subsequent Click Chemistry
Santosh B. Salunke,b,c N.Seshu Babua,c and Chien-Tien Chena∗
a
Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan
b
National Taiwan Normal University, Taipei, Taiwan
c
Santosh B.Salunke and N.Seshu Babu made equal contributions to this work
e-mail: [email protected]
SUPPORTING INFORMATION
Detailed procedures for FeCl3 catalyzed azido glycosylation and analytical data of
azido glycosides 1-10; Detailed procedures for FeCl3:Cu catalyzed dipolar
cycloaddition and analytical data for glycosyl 1,2,3-triazole conjugates 11-16;
procedure for one pot synthesis of 17; 1H and 13C NMR spectra for 1-17 (63 pages).
Table of Content
General experimental methods, Caution, and Attention------------------------------S2-S3
Table S1: Effect of solvents on the azido glycosylation of β-glucose peracetate------S4
Detailed procedure for FeCl3 catalyzed azido glycosylation and analytical data for
azido glycosides 1-10--------------------------------------------------------------------S4-S18
Table S2: Optimization of FeCl3/Cu(0) ratio for cyclo-addition reaction (i. e. click
chemistry) between β-azido glucose and 2-phenylethyne-------------------------------S19
Table S3: Control experiments for cycloaddition reactions between β-azido glucose
and 2-phenylethyne by using Sharpless and Fokin’s reagents--------------------S19-S20
Table S4: Control experiments for cycloaddition reactions between β-azido glucose
and 2-phenylethyne by using bimetallic catalyst Cu(OTf)2:Cu system----------------S20
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Detailed procedure for FeCl3:Cu catalyzed dipolar cycloaddition and analytical data
for glycosyl 1,2,3-triazole conjugates 11-16-----------------------------------------S20-S29
Procedure for one pot synthesis of glycosyl 1,2,3-triazole conjugate 17------- S29-S31
References------------------------------------------------------------------------------- S31-S33
1
H and 13C NMR spectra’s for 1-17---------------------------------------------------S34-S67
General. 1H NMR and
13
13
C NMR spectra were recorded on 400 MHz 1H (100 MHz
C) spectrometers in deuterochloroform with chloroform as an internal reference
unless otherwise stated. Chemical shifts are reported in ppm (δ). Coupling constants,
J, are reported in Hz. Electrospray ionization (ESI) mass spectra were recorded with
data reported in the form m/e (intensity relative to base peak). Analytical TLC was
performed on silica gel glass plates. Visualization was accomplished with UV light or
with phosphomolybdic acid (PMA) and KMnO4 staining agents. Column (flash)
chromatography was performed using 32-63 μm silica gels. THF and toluene were
dried over Na with benzophenone-ketyl intermediate under nitrogen atmosphere and
distilled before use. DMF, CH2Cl2 and CHCl3 were dried over CaH and distilled
before use. MeOH was dried over magnesium turnings under nitrogen atmosphere and
distilled before use. Oxygen was purged in CHCl3 before use. All reaction products
were isolated as chromatographically pure materials. All reagents and catalysts used
for azido glycosylation reaction were purchased from Across Organics. The acetate
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derivatives of glucose1, glactose2, mannose3, ribose, xylose4, maltose, lactose5,
maltotriose6 were synthesized by using 2 equiv of acetic anhydride (for each hydroxyl
group) in the presence of 10 mol% of Sodium acetate under reflux condition.
N-protected glucosamine derived substrates and propargyl-O-linked glucose
peracetate7 were synthesized by using literature methods.
Caution: Organic azides (e.g. TMSN3) are potentially explosive and corrosive
compounds and should be handled with great care,8 despite we did not sense any
adverse effects during our studies at small scale reactions.
Attention: It has been documented in the literatures that, ionic azides react with
CH2Cl2 to form explosive azidochloromethane and/or diazidomethane.9 It has been
noted that, if these azides were formed, they would be converted to stable triazole
derivatives in the subsequent azide-alkyne cycloaddition reactions. However, we did
not observe these side products under our catalytic conditions.
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Table S1. Effect of solvents on the azido glycosylation of glucose β-peracetate.a
OAc
AcO
AcO
O
OAc
OAc
OAc
TMSN3
Solvent (1 mL)
O
AcO
AcO
1
N3
OAc
Entry
Solvent
Time (h)
Conversion (%)b
Yield (%)c
1
CH3CN
36
5
n.d.
2
CH3COCH3
36
0
--
3
CH3NO2
36
decomposed
--
4
THF
36
0
--
5
TBME
40
55
47
6
toluene
40
95
86
toluene
7
quantitative
91
CH2Cl2
6
quantitative
96
7
d
8
a
5 mol% FeCl3
Carried out by using TMSN3 (0.38 mmol, 1.5 equiv), 5 mol% FeCl3 catalyst in 1
mL of solvent. bConversion of β-D-glucose peracetate was determined by 1H NMR
analysis of the crude reaction mixture. cIsolated, purified yield. dReaction was
conducted at 70 °C .
(A) Detailed procedures for FeCl3 catalyzed azido glycosylation and analytical
data of azido glycosides 1-10.
2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-glucopyranosyl azide (1).10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3R,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
(97.5 mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been
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stirred for 5 min at ambient temperature, a solution of trimethyl silyl azide i.e. TMSN3
(50 μL, 44 mg, 0.38 mmol, 1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The
resulting reaction mixture was stirred at ambient temperature and the progress of the
reaction was monitored by TLC. After complete consumption of starting material in 6
h, the reaction mixture was quenched with saturated aqueous NaHCO3 solution (5
mL). Two layers were separated and the aqueous layer was extracted with CH2Cl2 (2
× 3 mL). The combined organic layers were washed with brine (5 mL), dried
(MgSO4), filtered and evaporated under reduced pressure. The crude reside was
purified by column chromatography (EtOAc/hexanes, 1/2) on silica gel to afford 89
mg (96%) of 2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-glucopyranosyl azide 1 as a white
solid. 1H NMR (400 MHz, CDCl3) δ 5.19 (t, J = 9.2, 1H), 5.07 (t, J = 10, 1H), 4.92 (t,
J = 9.2, 1H), 4.63 (d, J = 8.8, 1H), 4.25 (dd, J = 12.4, 4.8, 1H), 4.14 (dd, J = 12.4, 2,
1H), 3.80-3.76 (m, 1H), 2.07 (s, 3H, COCH3), 2.05 (s, 3H, COCH3), 2.00 (s, 3H,
COCH3), 1.98 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3) δ 170.5, 170.0, 169.2,
169.1, 87.8, 74.0, 72.5, 70.6, 67.9, 61.6, 20.6, 20.4; MS ESI (C14H19O9N3, 373): 396
(M+Na+, 100); TLC Rf 0.34 (EtOAc/hexanes, 1/2); m.p. 124-125 °C (lit.11 m.p. 127
°C); [α]25D -30.2 (c 1.0, CHCl3) (lit.10 [α]23D -31 (c 1.0, CHCl3)).
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2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-galactopyranosyl azide (2).10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125
mmol, 0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A
solution of (2S,3S,4S,5R,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl
tetraacetate (97.5 mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After
having been stirred for 5 min at ambient temperature, a solution of TMSN3 (50 μL, 44
mg, 0.38 mmol, 1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting
reaction mixture was stirred at ambient temperature and the progress of the reaction
was monitored by TLC. After complete consumption of starting material in 6 h, the
reaction mixture was quenched with saturated aqueous NaHCO3 solution (5 mL). Two
layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL).
The combined organic layers were washed with brine (5 mL), dried (MgSO4), filtered
and evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 1/2) on silica gel to afford 89 mg (96%) of
2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-galactopyranosyl azide 2 as a white solid. 1H
NMR (400 MHz, CDCl3) δ 5.41 (d, J = 2.4, 1H), 5.15 (dd, J = 10, 8.8, 1H), 5.02 (dd,
J = 10.4, 3.6, 1H), 4.59 (d, J = 8.8, 1H), 4.18-4.14 (m, 2H), 4.00 (td, J = 6.8, 0.6, 1H),
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2.16 (s, 3H, COCH3), 2.08 (s, 3H, COCH3), 2.05 (s, 3H, COCH3), 1.98 (s, 3H,
COCH3); 13C NMR (100 MHz, CDCl3) δ 170.3, 170.0, 169.9, 169.2, 88.1, 72.7, 70.6,
67.95, 66.8, 61.2, 20.5, 20.4, 20.35; MS ESI (C14H19O9N3, 373): 396 (M+Na+, 100);
TLC Rf 0.35 (EtOAc/hexanes, 1/2); m.p. 95-97 °C (lit.11 m.p. 94-95 °C); [α]25D -15.4 (c
1.0, CHCl3) (lit.10 [α]23D -14 (c 1.0, CHCl3)).
2,3,4,6-tetra-O-acetyl-6-deoxy-α-D-mannopyranosyl azide (3).12
AcO
AcO
AcO
OAc
O
OAc
TMSN3
5 mol% FeCl3
CH2Cl2 (1 mL)
rt, 7 h
OAc
O
AcO
AcO
AcO
3
N3
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125
mmol, 0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A
solution
of
(3S,4S,5S,6R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl
tetraacetate (97.5 mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After
having been stirred for 5 min at ambient temperature, a solution of TMSN3 (50 μL, 44
mg, 0.38 mmol, 1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting
reaction mixture was stirred at ambient temperature and the progress of the reaction
was monitored by TLC. After complete consumption of starting material in 7 h, the
reaction mixture was quenched with saturated aqueous NaHCO3 solution (5 mL). Two
layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL).
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The combined organic layers were washed with brine (5 mL), dried (MgSO4), filtered
and evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 1/2) on silica gel to afford 83 mg (89%) of
2,3,4,6-tetra-O-acetyl-6-deoxy-α-D-mannopyranosyl azide 3 as a white solid. 1H
NMR (400 MHz, CDCl3) δ 5.37 (d, J = 1.5, 1H), 5.28-5.20 (m, 2H), 5.13 (t, J =2.3,
1H), 4.28 (dd, J = 12.4, 5.5, 1H), 4.16-4.11 (m, 2H), 2.18 (s, 3H, COCH3), 2.14 (s, 3H,
COCH3), 2.1 (s, 3H, COCH3), 2.05 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3)
δ 170.5, 169.8, 169.7, 169.6, 87.4, 70.6, 69.1 68.2, 65.6, 62.1, 20.7, 20.61, 20.6, 20.5;
MS ESI (C14H19O9N3, 373): 396 (M+Na+, 100); TLC Rf 0.32 (EtOAc/hexanes, 1/2).
m.p. 103-105 °C (lit.13 m.p. 104.1-104.9 °C); [α]25D +181.1 (c 1.0, CHCl3) (lit.13 [α]23D
+184 (c 1.0, CHCl3)).
2,3,5-tri-O-acetyl-β-D-ribofurunosyl azide (4).14
O
OAc
AcO
AcO
OAc
TMSN3
O
5 mol% FeCl3
CH2Cl2 (1 mL)
rt, 1.5 h
AcO
N3
OAc
AcO
4
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (1.2 mg, 0.0075 mmol,
0.03 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (79.5 mg, 0.25
mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred for 5 min at
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ambient temperature, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol, 1.5 equiv) in
CH2Cl2 (0.25 mL) was added slowly. The resulting reaction mixture was stirred at
ambient temperature and the progress of the reaction was monitored by TLC. After
complete consumption of starting material in 1.5 h, the reaction mixture was
quenched with saturated aqueous NaHCO3 solution (5 mL). Two layers were
separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined
organic layers were washed with brine (5 mL), dried (MgSO4), filtered and
evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 1/2) on silica gel to afford 72 mg (96%) of
2,3,5-tri-O-acetyl-β-D-ribofurunosyl azide 4 as a colorless oil. 1H NMR (400 MHz,
CDCl3) δ 5.33 (d, J = 1.4, 1H), 5.30 (dd, J = 6.6, 5.0, 1H), 5.10 (dd, J = 4.8, 1.6, 1H),
4.38 (dd, J = 12, 3.2, 1H), 4.34-4.30 (m, 1H), 4.12 (dd, J = 12.2, 4.2, 1H), 2.092 (s,
3H, COCH3), 2.09 (s, 3H, COCH3), 2.04 (s, 3H, COCH3);
13
C NMR (100 MHz,
CDCl3) δ 170.5, 169.5, 169.3, 92.6, 79.3, 74.4, 70.4, 62.9, 20.6, 20.4, 20.3; MS ESI
(C11H15O7N3, 301): 324 (M+Na+, 100); TLC Rf 0.34 (EtOAc/hexanes, 1/2); [α]25D
+111.3 (c 1.0, CHCl3) (lit.14 [α]23D +116 (c 1.0, CHCl3)).
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2,3,5-tri-O-acetyl-β-D-xylopyranosyl azide (5).10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (1.2 mg, 0.0075
mmol, 0.03 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A
solution of (2S,3S,4S)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (79.5 mg, 0.25
mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred for 5 min at
ambient temperature, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol, 1.5 equiv) in
CH2Cl2 (0.25 mL) was added slowly. The resulting reaction mixture was stirred at
ambient temperature and the progress of the reaction was monitored by TLC. After
complete consumption of starting material in 3 h, the reaction mixture was quenched
with saturated aqueous NaHCO3 solution (5 mL). Two layers were separated and the
aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined organic layers
were washed with brine (5 mL), dried (MgSO4), filtered and evaporated under
reduced pressure. The crude reside was purified by column chromatography
(EtOAc/hexanes, 1/2) on silica gel to afford 69 mg (92%) of 2,3,5-tri-O-acetyl-β-Dxylopyranosyl azide 5 as a white solid. 1H NMR (400 MHz, CDCl3) δ 5.18 (t, J = 8.8,
1H), 5.00-4.95 (m, 1H), 4.87 (t, J = 8.4, 1H), 4.63 (d, J = 8.0, 1H), 4.21 (dd, J = 12,
5.6, 1H), 3.44 (dd, J = 11.6, 9.2, 1H), 2.07 (s, 3H, COCH3), 2.042 (s, 3H, COCH3),
2.04 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3) δ 169.9, 169.7, 169.3, 88.3, 71.5,
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70.4, 68.4, 64.3, 20.6, 20.6; MS ESI (C11H15O7N3, 301): 324 (M+Na+, 100); TLC Rf
0.34 (EtOAc/hexanes, 1/2); m.p. 84-85 °C (lit.15 m.p. 87 °C); [α]25D +88.4 (c 1.0,
CHCl3) (lit.15 [α]25D +86 (c 1.0, CHCl3)).
2,3,6-tri-O-acetyl-4-O-( 2’,3’,4’,6’-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-glucopyranosylazide (6).10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3S,4S,6R)-6-(acetoxymethyl)-5-((2S,3S,4S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)
tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate (169.5 mg,
0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred for 5
min at ambient temperature, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol, 1.5
equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting reaction mixture was
stirred at ambient temperature and the progress of the reaction was monitored by TLC.
After complete consumption of starting material in 24 h, the reaction mixture was
quenched with saturated aqueous NaHCO3 solution (5 mL). Two layers were
separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined
organic layers were washed with brine (5 mL), dried (MgSO4), filtered and
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evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 149 mg (90%) of
2,3,6-tri-O-acetyl-4-O-(2’,3’,4’,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-glucopyr
-anosyl azide 6 as a amorphous solid. 1H NMR (400 MHz, CDCl3) δ 5.34 (d, J = 3.6,
1H), 5.20 (t, J = 9.4, 1H), 5.09 (dd, J = 10.4, 8, 1H), 4.94 (dd, J = 10.4, 3.6, 1H), 4.85
(t, J = 9.6, 1H), 4.62 (d, J = 8.8, 1H), 4.52-4.46 (m, 2H), 4.14-4.05 (m, 3H), 3.87 (t, J
= 6.8, 1H), 3.81 (t, J = 9.6, 1H), 3.70-3.71 (m, 1H), 2.14 (s, 3H, COCH3), 2.13 (s, 3H,
COCH3), 2.08 (s, 3H, COCH3), 2.06 (s, 3H, COCH3), 2.05 (s, 3H, COCH3), 2.04 (s,
3H, COCH3), 1.95 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3) δ 170.3, 170.1,
170.0, 169.6, 169.5, 169.1, 101.1, 87.7, 75.7, 74.8, 72.5, 71.0, 70.9, 70.7, 69.0, 66.6,
61.7, 60.8, 20.8, 20.7, 20.6, 20.5; MS ESI (C26H35O17N3, 661): 684 (M+Na+, 100);
TLC Rf 0.20 (EtOAc/hexanes, 1/1); [α]25D -21.2 (c 1.0, CHCl3) (lit.10 [α]23D -20.4 (c 1.0,
CHCl3)).
2,3,6-tri-O-acetyl-4-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucop
yranosylazide (7).10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
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(2S,3S,4S,5R,6R)-6-(acetoxymethyl)-5-((3S,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymet
hyl)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate (169.5 mg,
0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred for 5
min at ambient temperature, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol, 1.5
equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting reaction mixture was
stirred at ambient temperature and the progress of the reaction was monitored by TLC.
After complete consumption of starting material in 22 h, the reaction mixture was
quenched with saturated aqueous NaHCO3 solution (5 mL). Two layers were
separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined
organic layers were washed with brine (5 mL), dried (MgSO4), filtered and
evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 152 mg (92%) of
2,3,6-tri-O-acetyl-4-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyra
-nosyl azide 7 as a white solid. 1H NMR (400 MHz, CDCl3) δ 5.40 (d, J = 4, 1H), 5.35
(t, J = 10, 1H), 5.26 (t, J = 9.0, 1H), 5.05 (t, J = 9.8, 1H), 4.85 (dd, J = 10.8, 4.0, 1H),
4.78 (t, J = 8.8, 1H), 4.70 (d, J = 8.8, 1H), 4.51 (dd, J = 12, 2.4, 1H), 4.26-4.24 (m,
12.4, 2H), 4.07-4.03 (m, 2H), 4.01-3.99 (m, 1H), 3.79-3.70 (m, 1H), 2.15 (s, 3H,
COCH3), 2.10 (s, 3H, COCH3), 2.05 (s, 3H, COCH3), 2.04 (s, 3H, COCH3), 2.02 (s,
3H, COCH3), 2.01 (s, 3H, COCH3), 2.00 (s, 3H, COCH3);
13
C NMR (100 MHz,
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CDCl3) δ 170.4, 170.3, 169.9, 169.8, 169.3, 169.3, 95.6, 77.3, 77.0, 76.7, 74.9, 72.3,
71.4, 69.9, 69.1, 68.5, 67.9, 62.4, 61.4, 20.7, 20.6, 20.5, 20.4; MS ESI (C26H35O17N3,
661): 684 (M+Na+, 100); TLC Rf 0.15 (EtOAc/hexanes, 1/1); m.p. 181-183 °C (lit.16a
m.p. 180-182 °C); [α]25D -32.1 (c 1.0, CHCl3) (lit.16b [α]24D -31 (c 1.0, CHCl3)).
2,3,4,6-tetra-O-acetyl-6-deoxy-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-6-deo
xy-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-6-deoxy-β-D-glucopyranosyl
azide (8).17
AcO
AcO
OAc
O
AcO
O
AcO
OAc
TMSN3
O
OAc
AcO
O
AcO
O
AcO
5 mol% FeCl3
CH2Cl2 (1 mL)
rt, 28 h
AcO
AcO
OAc
O
AcO
O
AcO
OAc
O
OAc
AcO
O
AcO
OAc
8
O
N3
AcO
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-((2R,3R,4S,5R,6R)-3,4-diacetoxy-6-(acetoxym
ethyl)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2
-yloxy)tetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate (241.5
mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred
for 5 min at ambient temperature, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol,
1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting reaction mixture was
stirred at ambient temperature and the progress of the reaction was monitored by TLC.
After complete consumption of starting material in 28 h, the reaction mixture was
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quenched with saturated aqueous NaHCO3 solution (5 mL). Two layers were
separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined
organic layers were washed with brine (5 mL), dried (MgSO4), filtered and
evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 206 mg (87%) of
2,3,4,6-tetra-O-acetyl-6-deoxy-α-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-6-deoxyα-D-glucopyranosyl-(1-4)-2,3,6-tri-O-acetyl-6-deoxy-β-D-glucopyranosyl azide 8 as
a white solid. 1H NMR (400 MHz, CDCl3) δ 5.37-5.32 (m, 2H), 5.32 (d, J = 6.4, 1H),
5.25-5.21 (m, 2H), 5.03 (t, J = 9.8, 1H), 4.82 (dd, J = 10.4, 4.0, 1H), 4.76-4.67 (m,
3H), 4.49-4.41 (m, 2H), 4.29 (dd, J = 12.2, 4.4, 1H), 4.21 (dd, J = 12.4, 3.6, 1H), 4.15
(dd, J = 12.4, 3.2, 1H), 4.02 (dd, J = 12.4, 2.0, 1H), 3.96 (d, J = 9.2, 1H), 3.93-3.87
(m, 3H), 3.81-3.79 (m, 1H), 2.15 (s, 3H, COCH3), 2.12 (s, 3H, COCH3), 2.06 (s, 3H,
COCH3), 2.02 (s, 3H, COCH3), 2.0 (s, 6H, COCH3), 1.98 (s, 3H, COCH3), 1.97 (s, 6H,
2 × COCH3), 1.96 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3) δ 170.5, 170.4,
170.3, 170.4, 170.2, 169.7, 169.6, 169.4, 169.3, 95.8, 95.6, 87.3, 74.8, 74.0, 73.4, 72.4,
71.6, 71.4, 70.3, 70.0, 69.2, 69.0, 68.4, 67.8, 62.6, 62.2, 61.3, 20.8, 20.7, 20.5, 20.5,
20.4; MS ESI (C38H51O25N3, 949): 972 (M+Na+, 100); TLC Rf 0.10 (EtOAc/hexanes,
1/1); m.p. 95-96 °C; [α]25D +69.2 (c 1.0, CHCl3) (lit.17b [α]25D +65 (c 1.2, CHCl3)).
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3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide (9).18
OAc
O
AcO
AcO
O
N
OAc
N3
O
TMSN3
5 mol% FeCl3
O
AcO
AcO
N
O
CH2Cl2 (1 mL)
rt, 22 h
N3
O
9
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyra
n-2,4,5-triyl triacetate (119 mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added.
After having been stirred for 5 min at ambient temperature, a solution of TMSN3 (50
μL, 44 mg, 0.38 mmol, 1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The
resulting reaction mixture was stirred at ambient temperature and the progress of the
reaction was monitored by TLC. After complete consumption of starting material in
22 h, the reaction mixture was quenched with saturated aqueous NaHCO3 solution (5
mL). Two layers were separated and the aqueous layer was extracted with CH2Cl2 (2
× 3 mL). The combined organic layers were washed with brine (5 mL), dried
(MgSO4), filtered and evaporated under reduced pressure. The crude reside was
purified by column chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 105
mg (91%) of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 9 as
a white solid. 1H NMR (400 MHz, CDCl3) δ 7.87 (dd, J = 5.4, 3.0, 2H), 7.76 (dd, J =
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5.5, 3.0, 2H), 5.80 (dd, J = 10.5, 9.2, 1H), 5.65 (d, J = 9.4, 1H), 5.19 (t, J = 9.7, 1H),
4.35 (dd, J = 4.7, 12.4, 1H), 4.24 (dd, J = 12.5, 2.3, 1H), 4.24 (dd, J = 10.6, 9.2, 1H),
3.99-3.96 (m, 1H), 2.12 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 1.86 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3) δ 170.6, 169.9, 169.3, 134.5, 131.2, 123.7, 73.9, 85.5,
70.4, 68.4, 61.7, 53.1, 20.6, 20.5, 20.3; MS ESI (C20H20O9N4, 460): 483 (M+Na+,
100); TLC Rf 0.28 (EtOAc/hexanes, 1/1); m.p. 135-137 °C (lit.18a m.p. 135-138 °C);
[α]25D +39.6 (c 1.0, CHCl3) (lit.18b [α]25D +38 (c 1.0, CHCl3)).
3,4,6-tri-O-acetyl-2-N-acetyl-2-deoxy-β-D-glucopyranosyl azide (10).10
OAc
AcO
AcO
O
OAc
NHAc
TMSN3
20 mol% FeCl3
CH2Cl2 (1 mL)
rt, 72 h
OAc
O
AcO
AcO
N3
NHAc
10
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (8 mg, 0.05 mmol, 0.2
equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3R,4R,5S,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl
triacetate (97 mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having
been stirred for 5 min at ambient temperature, a solution of TMSN3 (50 μL, 44 mg,
0.38 mmol, 1.5 equiv) in CH2Cl2 (0.25 mL) was added slowly. The resulting reaction
mixture was stirred at ambient temperature and the progress of the reaction was
monitored by TLC. After complete consumption of starting material in 72 h, the
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reaction mixture was quenched with saturated aqueous NaHCO3 solution (5 mL). Two
layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL).
The combined organic layers were washed with brine (5 mL), dried (MgSO4), filtered
and evaporated under reduced pressure. The crude reside was purified by column
chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 86 mg (93%) of
3,4,6-tri-O-acetyl-2-N-acetyl-2-deoxy-β-D-glucopyranosyl azide 10 as a white solid.
1
H NMR (400 MHz, CDCl3) δ 6.09 (d, J = 8.8, 1H, NH), 5.25 (t, J = 10, 1H), 5.08 (t,
J = 9.6, 1H), 4.78 (d, J = 9.2, 1H), 4.25 (dd, J = 4.8, 12.4, 1H), 4.16-4.13 (m, 1H),
3.91 (dd, J = 19.4, 9.3, 1H), 3.81 (m, 1H), 2.09 (s, 3H, COCH3), 2.024 (s, 3H,
COCH3), 2.02 (s, 3H, COCH3), 1.97 (s, 3H, COCH3);
13
C NMR (100 MHz, CDCl3)
δ 170.9, 170.7, 170.6, 169.3, 88.3, 76.7, 73.9, 72.1, 68.1, 61.9, 54.0, 23.1, 20.7, 20.6,
20.5; MS ESI (C14H20O8N4, 372): 395 (M+Na+, 100); TLC Rf 0.20 (EtOAc/hexanes,
25
23
1/1); m.p. 161-162 °C (lit.19 m.p. 158-161 °C); [α] D -45.9 (c 1.0, CHCl3) (lit.10 [α] D
-47.7 (c 1.0, CHCl3)).
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Table S2: Optimization of FeCl3/Cu(0) ratio for cycloaddition reactions (i. e. click
chemistry) between β-azido glucose and 2-phenylethyne.a
Entry
FeCl3
mol%
Cu powder
mol%
FeCl3:Cu ratio
Time, h
Yield (%)
1
2
3
4
5
6
20
0
20
20
20
20
0
100
20
30
40
100
1:0
0:1
1:1
1:1.5
1:2
1:5
48
48
48
48
40
10
No reaction
No reaction
No reaction
Sluggish reaction
92
94
a
Reaction details: β-azido glucose (0.25 mmol, 1 equiv), 2-phenylethyne (0.375
mmol, 1.5 equiv) in t-BuOH:H2O (2 mL:1 mL). bIsolated yield after purification by
silica gel column chromatography .
Table S3: Control experiments for cycloaddition reactions between β-azido
glucose and 2-phenylethynea by using Sharpless and Fokin’s reagents.20
Entry
CuSO4
(mol%)
sodium ascorbate
(mol%)
CuSO4: sodium
ascorbate ratio
1
2
3
4
5
3
20
20
20
20
30
40
40
100
100
1:10
1:2
1:2
1:5
1:5
a
Time Conversion
(h)
(%)b
48
20
70
20
70
8
7
30
15
45
Yield
(%)c
n.d.
n.d.
24d
n.d.
40
Reaction details: β-azido glucose (0.25 mmol, 1 equiv), 2-phenylethyne (0.375 mmol, 1.5
equiv) in t-BuOH:H2O (2 mL:1 mL). bConversion of β-azido glucose 1 was determined by 1H
NMR analysis of the crude reaction mixture. cIsolated yield after purification by silica gel
column chromatography. n.d. = not determined. dRemaining starting material was recovered.
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Table S4: Control experiments for cyclo-addition reaction between β-azido
glucose and 2-phenylethynea by using bimetallic catalyst Cu(OTf)2:Cu system.21
OAc
O
AcO
AcO
OAc
Cu(OTf)2: Cu Powder
N3
OAc
1 (0.25 mmol)
1.5 equiv
Solvent
ambient temperature
Entry
Cu(OTf)2
(mol%)
Cu Powder
(mol%)
Cu(OTf)2:
Cu(0) ratio
Solvent
1
2
3
4
10
10
10
10
10
50
10
50
1:1
1:5
1:1
1:5
CH3CN
CH3CN
t-BuOH:H2O
t-BuOH:H2O
a
O
AcO
AcO
N N
N
OAc
12
Time Conv.
(h)
(%)b
40
12
35
35
21
quant.
0
9
Yield
(%)c
16 d
92
n.d.
n.d.
Reaction details: β-azido glucose (0.25 mmol, 1 equiv), 2-phenylethyne (0.375 mmol, 1.5
equiv) in CH3CN (6 mL) or t-BuOH:H2O (2 mL:1 mL). bConversion of β-azido glucose 1 was
determined by 1H NMR analysis of the crude reaction mixture. cIsolated yield after purification
by silica gel column chromatography. n.d. = not determined. dRemaining starting material was
recovered.
(B) Detailed procedures for FeCl3:Cu catalyzed 1,3-dipolar cycloaddition and
analytical data for glycosyl 1,2,3-triazole conjugates 11-16.
Phenyl 2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-glucopyranosyl 1,2,3-triazole (11).22
In a 10 mL, round bottomed flask were placed 20 mol% of FeCl3 (8.1 mg, 0.05 mmol,
0.2 equiv) and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient temperature
for 5 min and a solution of 2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-gluco-pyranosyl azide
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1 (93 mg, 0.25 mmol, 1 equiv) in t-BuOH (1 mL) was added followed by addition of
ethynylbenzene (41 μL, 38 mg, 0.375 mmol, 1.5 equiv). The resulting reaction
mixture was stirred at ambient temperature and the progress of the reaction was
monitored by TLC. After complete consumption of starting material in 10 h, the
organic volatiles were removed under reduced pressure and the resulting mixture was
partitioned between H2O and CH2Cl2 (5 mL each). The organic layer was separated
and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined organic
layers were washed with brine (10 mL), dried (MgSO4), filtered, passed through
Celite bed to remove inorganic salts and concentrated under reduced pressure. The
resulting crude residue was purified by column chromatography (EtOAc/hexanes, 1/1)
on silica gel to afford 109 mg (92%) of phenyl 2,3,4,6-tetra-O-acetyl-6-deoxy-β-Dglucopyranosyl 1,2,3-triazole 11 as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.0 (s,
1H), 7.83 (d, J = 7.2, 2H), 7.43 (t, J = 7.2, 2H,), 7.36 (d, J = 7.6, 1H), 5.93 (d, J = 9.2,
1H), 5.52 (t, J = 9.4, 1H), 5.44 (t, J = 9.4, 1H), 5.27 (t, J = 9.6, 1H), 4.33 (dd, J = 12.6,
5.0, 1H), 4.16 (dd, J = 12.6, 1.8, 1H), 4.05-4.02 (m, 1H), 2.084 (s, 3H, COCH3), 2.08
(s, 3H, COCH3), 2.04 (s, 3H, COCH3), 1.88 (s, 3H, COCH3);
13
C NMR (100 MHz,
CDCl3) δ 170.5, 169.9, 169.4, 169.0, 148.5, 129.9, 128.9, 128.6, 125.9, 117.7, 85.8,
75.3, 72.7, 70.2, 67.7, 61.6, 20.7, 20.6, 20.5, 20.2; MS ESI (C22H25O9N3, 475): 498
(M+Na+, 100); TLC Rf 0.42 (EtOAc/hexanes, 1/1); m.p. 211-213 °C (lit.22b m.p.
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213-215 °C); [α]25D -54.5 (c 1.0, CHCl3) (lit.22c [α]20D -56.2 (c 1.0, CHCl3)).
Phenyl 3,4,6-tri-O-acetyl-2-N-acetyl-6-deoxy-β-D-glucopyranosyl 1,2,3-triazole
(12).
OAc
AcO
AcO
O
OAc
N3
NHAc
10
FeCl3:Cu powder (1:5)
t-BuOH:H2O (2:1)
rt, 12 h
AcO
AcO
O
N N
N
NHAc
12
In a 10 mL, round bottomed flask were placed 20 mol% of FeCl3 (8.1 mg, 0.05 mmol,
0.2 equiv) and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient temperature
for 5 min and a solution of 3,4,6-tri-O-acetyl-2-N-acetyl-2-deoxy-β-D-glucopyranosyl
azide 10 (93 mg, 0.25 mmol, 1 equiv) in t-BuOH (1 mL) was added followed by
addition of ethynylbenzene (41 μL, 38 mg, 0.375 mmol, 1.5 equiv). The resulting
reaction mixture was stirred at ambient temperature and the progress of the reaction
was monitored by TLC. After complete consumption of starting material in 12 h, the
organic volatiles were removed under reduced pressure and the resulting mixture was
partitioned between H2O and CH2Cl2 (5 mL each). The organic layer was separated
and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined organic
layers were washed with brine (10 mL), dried (MgSO4), filtered, passed through
Celite bed to remove inorganic salts and concentrated under reduced pressure. The
resulting crude residue was purified by column chromatography (EtOAc/hexanes, 1/1)
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on silica gel to afford 105 mg (89%) of phenyl 3,4,6-tri-O-acetyl-2-N-acetyl-6-deoxyβ-D-glucopyranosyl 1,2,3-triazole 13 as a off white solid. 1H NMR (400 MHz,
CDCl3/CD3OD) δ 8.04 (s, 1H), 7.52 (d, J = 7.3, 2H), 7.13 (t, J = 7.4, 2H), 7.05 (d, J =
7.2, 1H), 5.81 (d, J = 10, 1H), 5.19 (t, J = 10, 1H), 4.99 (t, J = 9.6, 1H), 4.36 (t, J =
10.2, 1H), 4.05 (dd, J = 12.4, 4.8, 1H), 3.89-3.82 (m, 2H), 1.79 (s, 3H), 1.787 (s, 3H,
COCH3), 1.76 (s, 3H, COCH3), 1.46 (s, 3H, COCH3);
13
C NMR (100 MHz,
CDCl3/CD3OD) δ 171.5, 170.6, 170.1, 169.4, 147.6, 129.2, 128.3, 128.0, 125.2, 118.7,
85.4, 74.2, 72.0, 67.8, 61.4, 52.6, 21.4, 19.7, 19.7, 19.6; MS ESI (C22H26O8N4, 474):
497 (M+Na+, 100); TLC Rf 0.40 (EtOAc/hexanes, 1/1); m.p. 228-229 °C; [α]25D -62.4
(c 1.0, CHCl3).
Phenyl 2,3,6-tri-O-acetyl-4-O-( 2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-βD-glucopyranosyl 1,2,3-triazole (13).22
In a 10 mL, round bottomed flask were placed 20 mol% of FeCl3 (8.1 mg, 0.05
mmol, 0.2 equiv) and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient
temperature for 5 min and a solution of 2,3,6-tri-O-acetyl-4-O-(2’,3’,4’,6’-tetra-Oacetyl-β-D-glucopyranosyl)-β-D-glucopyranosylazide 7 (165 mg, 0.25 mmol, 1 equiv)
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in t-BuOH (1 mL) was added followed by addition of ethynylbenzene (41 μL, 38 mg,
0.375 mmol, 1.5 equiv). The resulting reaction mixture was stirred at ambient
temperature and the progress of the reaction was monitored by TLC. After complete
consumption of starting material in 12 h, the organic volatiles were removed under
reduced pressure and the resulting mixture was partitioned between H2O and CH2Cl2
(5 mL each). The organic layer was separated and the aqueous layer was extracted
with CH2Cl2 (2 × 3 mL). The combined organic layers were washed with brine (10
mL), dried (MgSO4), filtered, passed through Celite bed to remove inorganic salts
and concentrated under reduced pressure. The resulting crude residue was purified
by column chromatography (EtOAc/hexanes, 3/2) on silica gel to afford 166 mg
(87%) of phenyl 2,3,6-tri-O-acetyl-4-O-( 2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl 1,2,3-triazole 13 as a off white solid. 1H NMR (400 MHz,
CDCl3) δ 7.92 (s, 1H), 7.81 (d, J = 7.6, 2H), 7.42 (t, J = 7.4, 2H), 7.34 (d, J = 7.4,
1H), 5.94 (d, J = 9.2, 1H), 5.51-5.36 (m, 4H), 5.07 (t, J = 9.8, 1H), 4.88 (dd, J = 10.8,
4, 1H), 4.49 (dd, J = 12.4, 2.0, 1H), 4.29-4.23 (m, 2H), 4.17 (t, J = 8.8, 1H), 4.08 (dd,
J = 12.6, 1.8, 1H), 4.02-3.99 (m, 2H), 2.12 (s, 3H, COCH3), 2.10 (s, 3H, COCH3),
2.07 (s, 3H, COCH3), 2.03 (s, 3H, COCH3), 2.01 (s, 3H, COCH3), 1.85 (s, 3H,
COCH3); 1.72 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3) δ 170.5, 170.5, 170.3,
169.9, 169.4, 169.3, 148.4, 129.9, 128.9, 128.6, 125.9, 95.9, 85.3, 75.4, 75.2, 72.5,
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70.8, 70.0, 69.2, 68.8, 67.9, 62.5, 61.5, 20.8, 20.7, 20.6, 20.6, 20.2; MS ESI
(C34H41O17N3, 763): 786 (M+Na+, 100); TLC Rf 0.21 (EtOAc/hexanes, 1/1); m.p.
170-171 °C; [α]25D -38.5 (c 1.0, CHCl3).
Phenyl 2,3,5-tri-O-acetyl-β-D-ribofuranosyl 1,2,3-triazole (14).22
In a 10 mL, round bottomed flask were placed 20 mol% of FeCl3 (8.1 mg, 0.05 mmol,
0.2 equiv) and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient temperature
for 5 min and a solution of 2,3,5-tri-O-acetyl-β-D-ribofurunosyl azide 4 (75 mg, 0.25
mmol, 1 equiv) in t-BuOH (1 mL) was added followed by addition of ethynylbenzene
(41 μL, 38 mg, 0.375 mmol, 1.5 equiv). The resulting reaction mixture was stirred at
ambient temperature and the progress of the reaction was monitored by TLC. After
complete consumption of starting material in 8 h, the organic volatiles were removed
under reduced pressure and the resulting mixture was partitioned between H2O and
CH2Cl2 (5 mL each). The organic layer was separated and the aqueous layer was
extracted with CH2Cl2 (2 × 3 mL). The combined organic layers were washed with
brine (10 mL), dried (MgSO4), filtered, passed through Celite bed to remove
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inorganic salts and concentrated under reduced pressure. The resulting crude residue
was purified by column chromatography (EtOAc/hexanes, 1/1) on silica gel to afford
97 mg (96%) of phenyl 2,3,5-tri-O-acetyl-β-D-ribofuranosyl 1,2,3-triazole 14 as a
colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.80 (d, J = 7.2, 2H), 7.40 ( t,
J = 7.6, 2H), 7.32 (d, J = 7.2, 1H), 6.18 (d, J = 3.6, 1H), 5.9 (dd, J = 4.8, 4.0, 1H),
5.63 (t, J = 5.4, 1H), 4.48 (dd, 8.2, 4.2, 1H), 4.40 (dd, J = 12.4, 2.8, 1H), 4.23 (dd, J =
12.4, 4, 1H), 2.10 (s, 6H, 2 × COCH3), 2.02 (s, 3H, COCH3);
13
C NMR (100 MHz,
CDCl3) δ 170.2, 169.3, 169.2, 148.0, 129.9, 128.8, 125.7, 118.8, 89.9, 80.0, 74.1, 70.6,
62.7, 20.5, 20.3, 20.2; MS ESI (C19H21O7N3, 403): 426 (M+Na+, 100); TLC Rf 0.43
(EtOAc/hexanes, 1/1); [α]25D +87.2 (c 1.0, CHCl3).
2,3,4,6-tetra-O-acetyl-(4’-ethylcarboxylate)-β-D-glucopyranosyl
1,2,3-triazole
(15).22
In a 10 mL, round bottomed flask, 20 mol% of FeCl3 (8.1 mg, 0.05 mmol, 0.2 equiv)
and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) were placed in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient temperature
for 5 min and a solution of 2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-gluco-pyranosyl azide
1 (93 mg, 0.25 mmol, 1 equiv) in t-BuOH (1 mL) was added followed by addition of
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ethyl propiolate (38 μL, 37 mg, 0.375 mmol, 1.5 equiv). The resulting reaction
mixture was stirred at ambient temperature and the progress of the reaction was
monitored by TLC. After complete consumption of starting material in 10 h, the
organic volatiles were removed under reduced pressure and the resulting mixture was
partitioned between H2O and CH2Cl2 (5 mL each). The organic layer was separated
and the aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined organic
layers were washed with brine (10 mL), dried (MgSO4), filtered, passed through
Celite bed to remove inorganic salts and concentrated under reduced pressure. The
resulting crude residue was purified by column chromatography (EtOAc/hexanes, 1/1)
on silica gel to afford 112 mg (95%) of 2,3,4,6-tetra-O-acetyl-(4’-ethyl
carboxylate)-β-D-glucopyranosyl 1,2,3-triazole 15 as a white solid. 1H NMR (400
MHz, CDCl3) δ 8.33 (s, 1H), 5.92 (d, J = 8.8, 1H), 5.46-5.37 (m, 2H), 5.24 (t, J = 9.6,
1H), 4.42 (q, J = 7.1, 2H), 4.31 (dd, J = 12.6, 5.0, 1H), 4.15 (dd, J = 12.8, 1.4, 1H),
4.03-4.0 (m, 1H), 2.08 (s, 3H, COCH3), 2.06 (s, 3H, COCH3), 2.02 (s, 3H, COCH3),
1.89 (s, 3H, COCH3), 1.41 (t, J = 7, 3H); 13C NMR (100 MHz, CDCl3) δ 170.4, 169.8,
169.3, 168.8, 160.1, 140.9, 126.0, 85.8, 75.3, 72.3, 70.4, 67.5, 61.5, 61.4, 20.6, 20.4,
20.0, 14.2; MS ESI (C19H25O11N3, 494): 517 (M+Na+, 100); TLC Rf 0.39
(EtOAc/hexanes, 1/1); m.p. 170-171 °C (lit.22d m.p. 172-174 °C); [α]25D -46.3 (c 1.0,
CHCl3) (lit.22d [α]25D -62 (c 0.2, CHCl3)).
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S28
2,3,4,6-tetra-O-acetyl-(4’-hydroxymethyl)-6-deoxy-β-D-glucopyranosyl
1,2,3-triazole (16).22
In a 10 mL, round bottomed flask were placed 20 mol% of FeCl3 (8.1 mg, 0.05 mmol,
0.2 equiv) and Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv) in 1:1 mixture of
t-BuOH:H2O (1 mL : 1 mL). The resulting mixture was stirred at ambient temperature
for 5 min and a solution of 2,3,4,6-tetra-O-acetyl-6-deoxy-β-D-gluco-pyranosyl azide
1 (93 mg, 0.25 mmol, 1 equiv) in t-BuOH (1 mL) was added followed by addition of
prop-2-yn-1-ol (22 μL, 21 mg, 0.375 mmol, 1.5 equiv). The resulting reaction mixture
was stirred at ambient temperature and the progress of the reaction was monitored by
TLC. After complete consumption of starting material in 12 h, the organic volatiles
were removed under reduced pressure and the resulting mixture was partitioned
between H2O and CH2Cl2 (5 mL each). The organic layer was separated and the
aqueous layer was extracted with CH2Cl2 (2 × 3 mL). The combined organic layers
were washed with brine (10 mL), dried (MgSO4), filtered, passed through Celite bed
to remove inorganic salts and concentrated under reduced pressure. The resulting
crude residue was purified by column chromatography (EtOAc/hexanes, 1/1) on silica
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S29
gel to afford 100 mg (93%) of 2,3,4,6-tetra-O-acetyl-(4’-hydroxymethyl) -6-deoxy-β1
D-glucopyranosyl 1,2,3-triazole 16 as a off white solid. H NMR (400 MHz, CDCl3) δ
7.84 (s, 1H), 5.89 (d, J = 8.4, 1H), 5.46-5.37 (m, 2H), 5.23 (t, J = 9.4, 1H), 4.74 (brs,
2H), 4.25 (dd, J = 12.6, 5, 1H), 4.10 (d, J = 12.4, 1H), 4.01-3.99 (m, 1H), 3.42 (brs,
1H), 2.021 (s, 3H, COCH3), 2.02 (s, 3H, COCH3), 1.98 (s, 3H, COCH3), 1.82 (s, 3H,
COCH3);
13
C NMR (100 MHz, CDCl3) δ 170.5, 169.9, 169.4, 169.0, 148.5, 120.2,
85.6, 75.0, 72.6, 70.3, 67.7, 61.5, 56.3, 20.6, 20.5, 20.4, 20.1; MS ESI (C17H23O10N3,
429): 452 (M+Na+, 100); TLC Rf 0.40 (EtOAc/hexanes, 1/1); m.p. 149-151 °C (lit.22d
m.p. 152-154 °C); [α]25D -9.1 (c 1.0, CHCl3) (lit.22c [α]20D -6 (c 1.0, CHCl3)).
(C) Procedure for one pot synthesis of 2,3,4,6-tetra-O-acetyl-4’-O-(2,3,4,6-tetra
-O- acetyl-6-deoxy-glucopyranose)-6-deoxy-β-D-glucopyranosyl triazole (17).22
OAc
OAc
AcO
AcO
O
OAc
1.5 equiv TMSN3,
OAc
OAc
5 mol% FeCl3
CH2Cl2 (1 mL)
rt, 6h
AcO
AcO
O
OAc
1
AcO
AcO
O
O
OAc
N3
FeCl3:Cu powder
(1:5)
t-BuOH:H2O (2:1)
rt, 12 h
OAc
AcO
AcO
O
N N
N
AcO
O
O
OAc
OAc
AcO
OAc
17
To a 10 mL, round bottomed flask was placed 5 mol% of FeCl3 (2 mg, 0.0125 mmol,
0.05 equiv) in anhydrous CH2Cl2 (0.5 mL) under nitrogen atmosphere. A solution of
(2S,3S,4S,5R)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (98
mg, 0.25 mmol, 1 equiv) in CH2Cl2 (0.25 mL) was added. After having been stirred
for 5 min, a solution of TMSN3 (50 μL, 44 mg, 0.38 mmol, 1.5 equiv) in CH2Cl2
(0.25 mL) was added slowly. The resulting reaction mixture was stirred at ambient
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S30
temperature and the progress of the reaction was monitored by TLC. After complete
consumption of starting material in 6 h as judged by TLC, the reaction mixture was
concentrated under reduced pressure and the resulting residue was dried in vacuo. The
residue was then suspended in a mixture of t-BuOH:H2O (1 mL: 1 mL). After having
been stirred for 5 min, a solution of 15 mol% of FeCl3 (6.0 mg, 0.0375 mmol, 0.15
equiv) and (3R,4S,5S,6R)-2-(acetoxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran
-3,4,5-triyl triacetate (145 mg, 0.375 mmol, 1.5 equiv) in t-BuOH (1 mL) was added
followed by addition of Cu(s) powder (16 mg, 0.25 mmol, 1.0 equiv). After having
been stirred for 12 h at ambient temperature, the organic volatiles were removed
under reduced pressure and the resulting mixture was partitioned between H2O and
CH2Cl2 (5 mL each). The organic layer was separated and the aqueous layer was
extracted with CH2Cl2 (2 × 3 mL). The combined organic layers were washed with
brine (10 mL), dried (MgSO4), filtered and passed through Celite bed to remove
inorganic salts. The organic layer was then concentrated under reduced pressure and
the resulting crude residue was purified by column chromatography (EtOAc/hexanes,
1/1) on silica gel to afford 171 mg (90%) of 17 as a white solid. 1H NMR (400 MHz,
CDCl3) δ 7.80 (s, 1H), 5.86 (d, J = 8.8, 1H), 5.42-5.39 (m, 2H), 5.23 (t, J = 9.6, 1H),
5.16 (t, J = 9.4, 1H), 5.08 (t, J = 9.6, 1H), 4.97 (td, J = 8.2, 1.2, 1H), 4.90 (d, J = 12.8,
1H), 4.79 (d, J = 12.8, 1H), 4.53 (d, J = 8.0, 1H), 4.31-4.25 (m, 2H), 4.19-4.10 (m,
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S31
1H), 4.02-3.98 (m, 1H), 3.76-3.72 (m, 1H), 2.10 (s, 3H, COCH3), 2.06 (s, 3H,
COCH3), 2.05 (s, 3H, COCH3), 2.02 (s, 3H, COCH3), 2.00 (s, 3H, COCH3), 1.96 (s,
3H, COCH3), 1.94 (s, 3H, COCH3), 1.88 (s, 3H, COCH3);
13
C NMR (100 MHz,
CDCl3) δ 170.7, 170.4, 170.2, 169.8, 169.4, 169.3, 169.0, 144.2, 121.9, 98.7, 75.2,
72.6, 72.4, 71.7, 71.0, 70.4, 68.3, 67.6, 61.8, 61.7, 61.4, 20.7, 20.6, 20.5, 20.5, 20.0;
MS ESI (C30H39O19N3, 745): 768 (M+Na+, 100); TLC Rf 0.33 (EtOAc/hexanes, 1/1);
m.p. 198-200 °C (lit.23 m.p. 199-199.5 °C); [α]25D -41.6 (c 1.0, CHCl3).
References:
(1) H. Bretting, G. Jacobs, I. Benecke, W.A. Koenig and J. Thiem, Carbohydr. Res.,
1985, 139, 225.
(2) (a) G. Hodosi and P. Kovac,Carbohydr. Res., 1997, 303, 239; (b) J.-P. Utille and
D. Gagnaire, Carbohydr. Res., 1982, 106, 43.
(3) H. Ishii, I. Kitagawa, K. Matsushita, K. Shirakawa and K. Tori, Tetrahedron Lett.,
1981, 22, 1529.
(4) J. Xue, Y. Pan and Z. Guo, Tetrahedron Lett., 2002, 43, 1599.
(5) A. Yoshida, T. Hayashi, N. Takeda, S. Oida and E. Ohki, Chem. Pharm. Bull.,
1981, 29, 1854.
(6) N. Thiebault, D. Lesur, P. Gode, V. Moreau and F. Djedaini-Pilard, Carbohydr.
Res., 2008, 343, 2719.
(7) (a) C.O. Kappe, Angew. Chem. Int. Ed. Engl., 2004, 43, 6250; (b) D. D. Heard and
R. Barker, J. Org. Chem., 1968, 33, 740.
8 (a) For a discussion on the hazards associated with azides, see: Prudent Practice for
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S32
Handling Hazardous Chemicals in Laboratories, National Academic Press,
Washington, DC, 1983, p. 87-88; (b) For human toxicity, see: The Merck Index, 12th
ed., Merck & Co., Rahway, NJ, 1996; p. 4818 and 8726.
9 (a) R. E. Conrow and W. D. Dean, Org. Process res. Dev., 2008, 12, 2285; (b) A. Hassner,
M. Stern and H. E. Gottlieb, J. Org. Chem., 1990, 55, 2304.
(10) F. D. Tropper, F. O. Andersson, S. Braun and R. Roy, Synthesis, 1992, 618.
(11) H. J. Berthold, S. Franke, J. Thiem and T. Schotten, J. Org.Chem., 2010, 75, 3859.
(12) H. Paulsen, Z. Gyorgydecik and M. Friedmann, Chem. Ber., 1974, 107, 1568.
(13) K.Slamova, P. Marhol, K. Bezouska, V. Kren, L. Lindkvist, S. G. Hansen and H. H.
Jensen, Bioorg. Med. Chem. Lett., 2010, 20, 4263.
(14) A. Stimac and J. Kobe, Carbohydr. Res., 1992, 232, 359.
(15) A. E. Meslouti, D. Beaupere, G. Demailly and R. Uzan, Tetrahedron Lett., 1994,
35, 3913.
(16) (a) X. Zheng, J. Morgan, S. K. Pandey, Y. Chen, E. Tracy, H. Baumann, J. R.
Missert, C. Batt, J. Jackson, D. A. Bellnier, B. W. Henderson, and R. K. Pandey, J.
Med. Chem., 2009, 52, 4306; (b) M. Tamura and H. Okai, Carbohydr. Res., 1984, 133,
207.
(17) (a) L. Marmuse, S. A. Nepogodiev and R. A. Field, Org. Biomol. Chem., 2005, 3,
2225; (b) S. A. Nepogodiev, S. Dedola, L. Marmuse, M. Y. Oliveira, and R. A.
Field, Carbohydr. Res., 2007, 342, 529.
(18) (a) A. Dan, M. Lergenmüller, M. Amano, Y. Nakahara, T. Ogawa and Y. Ito,
Chem. Eur. J., 1998, 4, 2182; (b) L. Szilagyi, and Z. Gyoergydeak, Carbohydr. Res.,
1985 , 143, 21.
(19) D. Macmillan, A. M. Daines, M. Bayrhuber and S. L. Flitsch, Org. Lett., 2002 , 4,
1467.
(20) (a) V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless, Angew. Chem.
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S33
Int. Ed. Engl., 2002, 41, 2596; (b) S. Dedola, D. L. Hughes, S. A. Nepogodiev, M.
Rejzek and R. A. Field, Carbohydr. Res., 2010, 345, 1123.
(21) S. K. Yousuf, S. C. Taneja and D. Mukherjee, J. Org. Chem., 2010, 75, 3097.
(22) (a) R. Kumar, P. R. Maulik and A.K. Misra, Glycoconj. J., 2008, 25, 595; (b) L.
L. Rossi and A. Basu, Bioorg. Med. Chem. Lett., 2005, 15, 3596; (c) S. Dedola, S. A.
Nepogodiev, M. Rejzek, R. A. Field and D. L. Hughes, Carbohyd. Res., 2010, 345,
1123; (d) Bokor, E. Somsak, L. Docsa, T. and Gergely, P. Bioorg. Med. Chem., 2010,
18, 1171.
(23) V. O. Rodionov, S. I. Presolski, S. Gardinier, Y. H. Lim and M. G. Finn, J. Am.
Chem. Soc., 2007, 129, 12696.
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
7.260
5.216
5.192
5.169
5.099
5.074
5.050
4.948
4.925
4.902
4.638
4.616
4.268
4.256
4.237
4.225
4.160
4.155
4.129
4.124
3.798
3.792
3.786
3.780
3.773
3.767
3.761
3.755
2.071
2.047
2.002
1.979
S34
F2 - Acquisition Parameters
Date_
20081204
Time
23.32
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
22
DW
83.400 usec
DE
6.50 usec
TE
299.9 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
OAc
O
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.798
3.792
3.786
3.780
3.773
3.767
3.761
3.755
4.268
4.256
4.237
4.225
4.160
4.155
4.129
4.124
OAc
4.948
4.925
4.902
5.216
5.192
5.169
5.099
5.074
5.050
1
N3
4.638
4.616
AcO
AcO
3.8
Current Data Parameters
NAME
B-001-L
EXPNO
6
PROCNO
1
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300091 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
8
7
6
5
4
3
2
3.000
3.012
3.009
3.025
9
1.048
1.046
1.087
1.043
1.058
1.073
1.032
10
1
1D NMR plot parameters
20.00
CY
15.15
F1P
2.087
F1
834.90
ppm CX
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
B-001-L
EXPNO
7
PROCNO
1
20.59
20.44
87.81
77.32
77.00
76.68
73.95
72.53
70.58
67.83
61.59
170.49
170.01
169.22
169.11
S35
F2 - Acquisition Parameters
Date_
20081204
Time
23.37
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
29
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
6.50 usec
TE
299.7 K
D1
1.50000000 sec
d11
0.03000000 sec
DELTA
1.39999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
OAc
O
AcO
AcO
1
N3
OAc
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127672 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
7.259
5.415
5.409
5.291
5.176
5.154
5.151
5.129
5.044
5.035
5.018
5.009
4.602
4.580
4.183
4.172
4.162
4.155
4.147
4.024
4.022
4.006
3.991
3.990
2.161
2.082
2.053
1.980
S36
Current Data Parameters
NAME
galactose azide-pure
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20090405
Time
19.50
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
128
DW
83.400 usec
DE
6.50 usec
TE
298.0 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
5.2
5.1
5.0
4.9
4.8
4.7
ppm
4.2
4.024
4.022
4.006
3.991
3.990
4.183
4.172
4.162
4.155
4.147
4.602
4.580
5.044
5.035
5.018
5.009
5.176
5.154
5.151
5.129
OAc OAc
O
N3
AcO
OAc
2
4.1
4.0
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300095 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
6
5
4
3
2
3.002
3.082
3.057
3.008
7
2.021
1.029
8
1.004
9
1.052
1.007
1.002
10
1
1D NMR plot parameters
20.00
CY
10.50
F1P
2.240
F1
896.10
ppm CX
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S37
OAc OAc
O
N3
AcO
OAc
2
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S38
OAc
O
AcO
AcO
AcO
3
N3
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S39
OAc
O
AcO
AcO
AcO
3
N3
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
7.259
5.336
5.332
5.314
5.301
5.297
5.285
5.112
5.108
5.100
5.096
4.399
4.391
4.369
4.361
4.339
4.329
4.322
4.313
4.304
4.139
4.128
4.108
4.098
2.092
2.089
2.040
S40
OAc
5.3
5.2
5.1 ppm
4.4
4.139
4.128
4.108
4.098
4
5.336
5.332
5.314
5.301
5.297
5.285
AcO
F2 - Acquisition Parameters
Date_
20090121
Time
13.56
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
1
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
57
DW
83.400 usec
DE
6.50 usec
TE
297.8 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
N3
4.399
4.391
4.369
4.361
4.339
4.329
4.322
4.313
4.304
AcO
5.112
5.108
5.100
5.096
O
Current Data Parameters
NAME
ribose-azide
EXPNO
1
PROCNO
1
4.3
4.2
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
8
7
6
5
4
3
2
6.045
3.009
9
1.005
1.018
1.002
10
1.021
1.012
1.000
F2 - Processing parameters
SI
16384
SF
400.1300088 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
1
ppm
1D NMR plot parameters
CX
20.00
CY
21.22
F1P
2.133
F1
853.54
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
O
AcO
AcO
4
Current Data Parameters
NAME
ribose-azide
EXPNO
2
PROCNO
1
20.56
20.39
20.34
92.56
79.28
77.32
77.00
76.68
74.37
70.37
62.91
170.47
169.45
169.31
S41
F2 - Acquisition Parameters
Date_
20090121
Time
14.00
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
62
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
6.50 usec
TE
297.8 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
N3
OAc
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127535 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
O
5.1
5.0
4.9
4.8
4.7
3.459
3.436
3.430
3.406
4.230
4.216
4.200
4.187
4.2
ppm
4.0
3.8
3.6
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300091 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
7
6
5
4
3
2
3.096
6.083
8
1.093
9
1.037
10
1.000
1.052
1.014
1.015
5.2
F2 - Acquisition Parameters
Date_
20081212
Time
20.32
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
203.2
DW
83.400 usec
DE
6.50 usec
TE
298.9 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
OAc
5.007
4.994
4.984
4.971
4.961
4.948
4.891
4.871
4.849
5.204
5.182
5.160
5
Current Data Parameters
NAME
xylose azide
EXPNO
1
PROCNO
1
N3
4.639
4.619
AcO
AcO
5.204
5.182
5.160
5.007
4.994
4.984
4.971
4.961
4.948
4.891
4.871
4.849
4.639
4.619
4.230
4.216
4.200
4.187
3.459
3.436
3.430
3.406
2.074
2.042
2.036
7.259
S42
1
ppm 1D NMR plot parameters
CX
CY
F1P
F1
20.00
10.50
5.373
2150.09
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
O
AcO
AcO
5
Current Data Parameters
NAME
nsp-triazole-clcl
EXPNO
2
PROCNO
1
20.61
20.55
88.32
77.32
77.00
76.68
71.54
70.43
68.43
64.28
169.94
169.68
169.25
S43
F2 - Acquisition Parameters
Date_
20081227
Time
22.21
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
182
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
6.50 usec
TE
302.9 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
N3
OAc
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127466 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
N3
OAc
6
4.6
4.5
5.2
5.1
5.0
4.9
ppm
4.140
4.130
4.124
4.118
4.112
4.096
4.090
4.073
4.063
4.045
3.883
3.865
3.849
3.831
3.806
3.783
3.714
3.709
3.701
3.697
3.689
3.684
3.677
3.672
4.515
4.510
4.484
4.464
4.630
4.608
5.3
4.4
4.3
4.2
4.1
4.0
3.9
3.8
3.7
Current Data Parameters
NAME
Lact azide-pure
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20100428
Time
15.46
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
114
DW
83.400 usec
DE
8.00 usec
TE
673.2 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
4.963
4.954
4.937
4.928
4.870
4.848
4.824
OAc
O
5.220
5.197
5.173
5.115
5.095
5.089
5.069
OAc OAc
O
O
AcO
OAc AcO
5.343
5.334
7.260
5.343
5.334
5.220
5.197
5.173
5.115
5.095
5.089
5.069
4.963
4.954
4.937
4.928
4.870
4.848
4.824
4.630
4.608
4.515
4.510
4.484
4.464
4.140
4.130
4.124
4.118
4.112
4.096
4.090
4.073
4.045
3.883
3.865
3.849
3.831
3.806
3.783
3.714
3.709
3.701
3.697
3.684
2.140
2.126
2.061
2.053
2.037
1.953
S44
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
3.6 ppm
F2 - Processing parameters
SI
16384
SF
400.1300091 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
8
7
6
5
4
3
2
3.088
3.063
3.028
3.005
6.076
3.000
9
1.050
1.011
1.010
1.017
1.024
1.017
2.003
3.096
1.024
0.996
0.999
10
1
ppm 1D NMR plot parameters
CX
CY
F1P
F1
20.00
11.96
2.194
877.95
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
OAc OAc
O
O
AcO
OAc AcO
6
OAc
O
Current Data Parameters
NAME
Lact azide-pure
EXPNO
2
PROCNO
1
20.75
20.68
20.58
20.45
101.07
87.67
77.32
77.00
76.69
75.74
74.77
72.50
70.96
70.90
70.73
69.04
66.56
61.70
60.76
170.31
170.08
170.01
169.60
169.45
169.05
S45
F2 - Acquisition Parameters
Date_
20100428
Time
15.47
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
97
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
8192
DW
19.900 usec
DE
8.00 usec
TE
673.2 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
N3
OAc
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6243390 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127690 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
4.5
4.4
4.3
4.2
5.3
5.2
5.1
4.872
4.862
4.845
4.835
4.803
4.782
4.759
4.714
4.692
5.0
4.9
4.8
4.1
4.0
3.9
3.8
Current Data Parameters
NAME
Maltose azide-pure
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20100331
Time
16.24
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
322.5
DW
83.400 usec
DE
6.50 usec
TE
297.8 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
ppm
4.065
4.059
4.035
4.028
4.012
3.989
3.968
3.962
3.954
3.943
3.937
3.928
3.800
3.793
3.789
3.782
3.776
3.769
3.765
3.758
4.263
4.259
4.254
4.248
4.232
4.222
4.218
4.524
4.518
4.494
4.487
5.4
5.074
5.050
5.025
5.410
5.400
5.373
5.349
5.323
5.295
5.279
5.256
5.234
7.260
5.410
5.400
5.373
5.349
5.323
5.279
5.256
5.234
5.074
5.050
5.025
4.872
4.862
4.845
4.835
4.803
4.782
4.759
4.714
4.692
4.524
4.518
4.494
4.487
4.263
4.259
4.254
4.248
4.232
4.222
4.218
4.065
4.059
4.035
4.028
4.012
3.989
3.962
3.937
3.793
3.789
2.152
2.099
2.047
2.037
2.022
2.008
1.998
S46
======== CHANNEL f1 ========
NUC1
1H
P1
9.70 usec
PL1
3.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300095 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
8
7
6
5
4
3
2
3.050
3.061
3.078
3.042
3.001
3.000
3.052
9
1.042
1.071
1.111
1.099
1.067
1.036
1.008
1.073
1.076
1.033
2.056
1.034
1.036
10
1
ppm 1D NMR plot parameters
CX
CY
F1P
F1
20.00
10.42
5.482
2193.37
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
pure
EXPNO
2
PROCNO
1
20.67
20.58
20.49
20.39
95.58
87.28
77.33
77.01
76.69
74.91
74.12
72.33
71.35
69.87
69.13
68.49
67.87
62.42
61.37
170.35
170.25
169.94
169.77
169.33
169.26
S47
F2 - Acquisition Parameters
Date_
20100410
Time
15.39
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
93
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
181
DW
19.900 usec
DE
8.00 usec
TE
673.2 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6243390 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
100.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127533 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
5.3
5.2
5.1
Current Data Parameters
NAME
PTHALIC-12PH-INDOL
EXPNO
6
PROCNO
1
F2 - Acquisition Parameters
Date_
20090321
Time
21.25
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
32
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
1.3664756 sec
ppm AQ
RG
40.3
DW
83.400 usec
DE
6.50 usec
TE
299.9 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
4.835
4.825
4.809
4.799
4.763
4.741
4.722
4.719
4.713
4.693
4.687
4.671
5.0
4.9
4.8
4.311
4.301
4.281
4.270
4.230
4.221
4.199
4.190
4.168
4.160
4.137
4.129
4.108
4.090
4.073
4.055
4.039
4.034
4.008
4.003
3.972
3.949
3.933
3.926
3.916
3.894
3.870
3.808
3.799
3.791
3.785
3.777
3.768
4.487
4.481
4.456
4.449
4.441
4.415
4.410
5.4
5.054
5.029
5.005
5.372
5.361
5.354
5.350
5.342
5.329
5.317
5.292
5.276
5.252
5.238
5.229
5.208
5.372
5.361
5.354
5.350
5.342
5.329
5.317
5.292
5.276
5.252
5.238
5.229
5.208
5.029
4.835
4.825
4.809
4.799
4.741
4.722
4.719
4.713
4.693
4.687
4.671
4.456
4.449
4.441
4.415
4.410
4.301
4.199
4.190
4.039
4.034
3.949
3.933
3.926
3.916
3.894
2.147
2.119
2.061
2.016
2.013
1.995
1.982
1.968
1.962
S48
4.7
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
10
4.4
9
4.3
8
4.2
7
4.1
4.0
6
3.9
5
3.8
4
F2 - Processing parameters
SI
16384
SF
400.1300091 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
ppm
3
2
2.030
1.057
2.033
1.048
1.022
3.066
2.023
1.012
1.062
1.007
1.030
1.124
3.056
1.028
3.054
3.029
3.012
6.200
3.016
3.090
9.008
4.5
1
1D NMR plot parameters
CX
20.00
10.50
ppm CY
F1P
2.281
F1
912.69
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
maltose azide
EXPNO
2
PROCNO
1
95.81
95.57
87.29
77.32
77.00
76.68
74.81
74.08
73.41
72.44
71.55
71.42
70.32
69.98
69.24
68.97
68.42
67.81
62.59
62.21
61.29
20.77
20.68
20.54
20.45
20.42
170.46
170.40
170.32
170.22
169.87
169.72
169.59
169.39
169.32
S49
F2 - Acquisition Parameters
Date_
20090323
Time
19.35
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
75
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
8192
DW
19.900 usec
DE
6.50 usec
TE
298.5 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127528 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S50
OAc
O
AcO
AcO
O
N
N3
O
9
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S51
OAc
O
AcO
AcO
O
N
N3
O
9
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
7.263
6.098
6.076
5.279
5.254
5.229
5.104
5.080
5.056
4.792
4.769
4.276
4.264
4.245
4.233
4.164
4.138
4.133
3.952
3.928
3.903
3.880
3.821
3.815
3.809
3.802
3.796
3.790
2.085
2.024
2.016
1.965
1.232
S52
NAME
EXPNO
PROCNO
Date_
Time
INSTRUM
PROBHD
PULPROG
TD
SOLVENT
NS
DS
SWH
FIDRES
AQ
RG
DW
DE
TE
D1
MCREST
MCWRK
OAc
O
4.3
8
5.2
5.0
7
4.2
4.1
4.0
3.9
3.8
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
SI
16384
SF
400.1300074 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
ppm
ppm
6
5
4
3
2
3.116
6.366
3.165
5.4
1.139
1.081
1.046
1.063
9
5.6
1.080
1.060
1.001
10
5.8
1.000
6.0
3.952
3.928
3.903
3.880
3.821
3.815
3.809
3.802
3.796
3.790
4.276
4.264
4.245
4.233
4.164
4.138
4.133
NHAc
5.279
5.254
5.229
5.104
5.080
5.056
6.098
6.076
10
N3
4.792
4.769
AcO
AcO
NH AC azide C13
1
1
20091218
21.49
spect
5 mm BBO BB-1H
zg30
16384
CDCl3
1
0
5995.204 Hz
0.365918 Hz
1.3664756 sec
90.5
83.400 usec
6.50 usec
297.2 K
1.50000000 sec
0.00000000 sec
0.01500000 sec
1
ppm
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
NH AC azide C13
EXPNO
2
PROCNO
1
23.13
20.66
20.57
20.52
88.33
77.32
77.21
77.00
76.68
73.86
72.12
68.11
61.85
54.01
170.90
170.67
170.58
169.27
S53
F2 - Acquisition Parameters
Date_
20091218
Time
21.50
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
98
DS
0
SWH
25062.656 Hz
FIDRES
0.382426 Hz
AQ
1.3074932 sec
RG
8192
DW
19.950 usec
DE
6.50 usec
TE
297.2 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
OAc
O
AcO
AcO
10
N3
NHAc
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6243390 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
100.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127513 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
7.8
7.7
7.6
7.5
7.4
4.350
4.337
4.318
4.306
5.7
5.6
5.5
5.4
5.294
5.270
5.246
5.548
5.524
5.501
5.465
5.441
5.418
5.8
7.448
7.430
7.411
7.368
7.349
7.331
7.842
7.824
5.9
5.3 ppm
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
4.3
4.2
4.1
4.0
Current Data Parameters
NAME
glucose triazole pur
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20090411
Time
20.58
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
161.3
DW
83.400 usec
DE
6.50 usec
TE
297.6 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
4.176
4.171
4.144
4.140
4.054
4.049
4.042
4.037
4.029
4.024
4.016
4.011
5.946
5.923
8.004
7.842
7.824
7.448
7.430
7.411
7.368
7.349
7.331
7.260
5.946
5.923
5.548
5.524
5.501
5.465
5.441
5.418
5.294
5.270
5.246
4.350
4.337
4.318
4.306
4.176
4.171
4.144
4.140
4.054
4.049
4.042
4.037
4.029
4.024
4.016
4.011
2.084
2.075
2.036
1.881
1.659
S54
ppm
F2 - Processing parameters
SI
16384
SF
400.1300095 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
6
5
4
3
2
3.092
3.075
3.027
3.011
7
1.036
1.056
1.024
8
1.014
1.012
1.012
1.041
9
1.000
2.008
2.006
1.026
10
1
ppm 1D NMR plot parameters
CX
CY
F1P
F1
20.00
10.50
2.155
862.43
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
dr-12
EXPNO
9
PROCNO
1
20.65
20.51
20.14
85.79
77.32
77.00
76.68
75.16
72.72
70.19
67.74
61.56
129.87
128.85
128.55
125.89
117.69
148.48
170.46
169.88
169.35
168.98
S55
F2 - Acquisition Parameters
Date_
20090307
Time
21.22
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
151
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
6.50 usec
TE
299.0 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127672 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
5.8
7.5
7.4
7.3
7.2
7.1
ppm
5.6
5.4
5.2
4.997
4.973
4.949
3.8
5.822
5.797
4.0
5.215
5.190
5.165
4.2
7.150
7.132
7.113
7.072
7.054
7.036
7.260
7.528
7.509
4.4
Current Data Parameters
NAME
NHac
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20090405
Time
17.49
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
MeOD
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
57
DW
83.400 usec
DE
6.50 usec
TE
298.0 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
4.073
4.061
4.042
4.030
3.896
3.864
3.846
3.831
3.827
3.821
4.263
4.390
4.365
4.339
8.035
7.528
7.509
7.260
7.150
7.132
7.113
7.072
7.054
7.036
5.822
5.797
5.215
5.190
5.165
4.997
4.973
4.949
4.390
4.365
4.339
4.263
4.073
4.061
4.042
4.030
3.896
3.864
3.846
3.831
3.827
3.821
1.788
1.787
1.763
1.455
S56
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
ppm
F2 - Processing parameters
SI
16384
SF
400.1301123 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
4
3
2
6.053
3.037
3.039
5
1.075
1.037
2.055
6
1.025
1.069
7
1.003
8
2.058
2.094
1.027
9
1.000
10
1
1D NMR plot parameters
20.00
CY
10.50
F1P
5.882
F1
2353.48
ppm CX
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
NHAc C13
EXPNO
4
PROCNO
1
85.39
77.32
77.00
76.68
74.19
72.00
67.75
61.38
52.62
48.58
48.37
48.16
47.94
47.73
47.52
47.30
21.38
19.73
19.65
19.58
129.23
128.33
128.03
125.22
118.65
147.59
171.45
170.64
170.10
169.39
S57
F2 - Acquisition Parameters
Date_
20090405
Time
18.28
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
108
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
8192
DW
19.900 usec
DE
6.50 usec
TE
298.0 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127934 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
4.510
4.505
4.479
4.474
4.298
4.286
4.268
4.260
4.238
4.229
4.191
4.167
4.145
4.095
4.090
4.063
4.059
4.027
4.021
4.002
3.996
3.970
7.923
7.823
7.804
7.439
7.421
7.402
7.360
7.341
7.260
5.950
5.927
5.484
5.463
5.454
5.436
5.412
5.406
5.389
5.381
5.356
5.098
5.073
4.904
4.894
4.877
4.867
4.505
4.479
4.474
4.286
4.268
4.260
4.238
4.229
4.167
4.145
4.095
4.090
4.063
4.059
4.002
3.996
2.123
2.103
2.066
2.030
2.009
1.853
1.721
S58
ppm
4.904
4.894
4.877
4.867
5.098
5.073
5.049
5.507
5.484
5.463
5.454
5.436
5.412
5.406
5.389
5.381
5.356
5.950
5.927
5.6
6
1.043
7
3.002
8
1.000
2.119
9
4.0
5.4
5.2
5
4
5.0
ppm
3
maltose triazole c13
9
1
20090307
21.56
spect
5 mm BBO BB-1H
zg30
16384
CDCl3
1
0
5995.204 Hz
0.365918 Hz
1.3664756 sec
114
83.400 usec
6.50 usec
299.1 K
1.50000000 sec
0.00000000 sec
0.01500000 sec
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
SI
16384
SF
400.1300089 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
ppm
5.8
10
4.1
2
3.134
3.080
3.086
6.047
3.153
3.052
7.4
4.2
6.020
7.5
1.145
7.6
4.3
1.027
1.056
7.7
4.4
4.081
7.8
7.439
7.421
7.402
7.360
7.341
7.323
7.823
7.804
4.5
NAME
EXPNO
PROCNO
Date_
Time
INSTRUM
PROBHD
PULPROG
TD
SOLVENT
NS
DS
SWH
FIDRES
AQ
RG
DW
DE
TE
D1
MCREST
MCWRK
1
ppm
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
maltose triazole c13
EXPNO
10
PROCNO
1
20.78
20.72
20.64
20.55
20.16
95.90
85.29
77.32
77.00
76.68
75.38
75.20
72.50
70.83
69.99
69.20
68.76
67.93
62.53
61.45
129.82
128.85
128.56
125.85
117.72
148.35
170.54
170.46
170.29
169.87
169.38
169.28
S59
F2 - Acquisition Parameters
Date_
20090307
Time
21.58
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
158
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
8192
DW
19.900 usec
DE
6.50 usec
TE
299.1 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127497 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
S60
5.9
5.8
5.7
ppm
4.246
4.236
4.215
4.205
6.0
4.495
4.485
4.474
4.463
4.422
4.415
4.391
4.384
7.419
7.401
7.381
7.336
7.318
7.300
7.260
7.812
7.809
7.791
6.1
F2 - Acquisition Parameters
Date_
20090314
Time
16.19
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
40.3
DW
83.400 usec
DE
6.50 usec
TE
299.9 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
5.640
5.627
5.613
5.906
5.896
5.894
5.884
6.185
6.176
7.957
7.812
7.809
7.791
7.419
7.401
7.381
7.336
7.318
7.300
7.260
6.185
6.176
5.906
5.896
5.894
5.884
5.640
5.627
5.613
4.495
4.485
4.474
4.463
4.422
4.415
4.391
4.384
4.246
4.236
4.215
4.205
2.099
2.024
Current Data Parameters
NAME
ribose triazole
EXPNO
1
PROCNO
1
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
7.6
7.5
7.4
ppm
4.5
8
7
6
1.011
1.010
1.015
9
1.000
2.016
2.048
1.001
10
4.4
5
4.3
4
F2 - Processing parameters
SI
16384
SF
400.1300088 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
ppm
3
2
6.075
3.038
7.7
1.029
1.088
1.090
7.8
1
1D NMR plot parameters
20.00
CY
10.50
F1P
8.128
F1
3252.12
ppm CX
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
PTHALIC-12PH-INDOL
EXPNO
3
PROCNO
1
20.49
20.30
20.23
89.92
80.77
77.32
77.00
76.68
74.14
70.57
62.69
129.89
128.75
128.32
125.65
118.77
147.99
170.23
169.32
169.17
S61
F2 - Acquisition Parameters
Date_
20090321
Time
20.57
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
68
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
6.50 usec
TE
300.2 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127604 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
4.165
4.162
4.134
4.130
4.039
4.034
4.027
4.022
4.014
4.009
4.002
4.445
4.428
4.410
4.392
4.328
4.315
4.296
4.284
5.455
5.432
5.410
5.391
5.367
5.261
5.236
5.213
5.933
5.911
1.422
1.405
1.387
8.333
7.259
5.933
5.911
5.455
5.432
5.410
5.391
5.367
5.261
5.236
5.213
4.445
4.428
4.410
4.392
4.328
4.315
4.296
4.284
4.165
4.162
4.134
4.130
4.039
4.034
4.027
4.022
4.014
4.009
4.002
3.997
2.081
2.063
2.023
1.885
1.422
1.405
1.387
S62
1.4
5.8
5.6
5.4
ppm
4.4
4.3
4.2
4.1
4.0
ppm
Current Data Parameters
NAME
NHac
EXPNO
2
PROCNO
1
F2 - Acquisition Parameters
Date_
20090405
Time
18.17
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
161.3
DW
83.400 usec
DE
6.50 usec
TE
298.0 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300095 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
5
4
3
2
3.000
3.014
3.007
3.004
3.076
6
2.072
1.096
1.101
1.100
7
2.017
1.058
8
1.033
9
1.000
10
1
NMR plot parameters
ppm 1D
CX
20.00 cm
CY
F1P
F1
10.50 cm
2.215 ppm
886.46 Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
propargy ester triazole
EXPNO
5
PROCNO
1
20.57
20.43
20.04
14.19
85.84
77.32
77.00
76.68
75.25
72.31
70.39
67.53
61.49
61.40
126.01
140.85
170.37
169.78
169.25
168.86
160.11
S63
F2 - Acquisition Parameters
Date_
20090404
Time
20.39
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
83
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
8192
DW
19.900 usec
DE
6.50 usec
TE
297.8 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6242995 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127520 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
5.8
5.6
5.4
Current Data Parameters
NAME
-propargy triazole
EXPNO
1
PROCNO
1
4.3
ppm
F2 - Acquisition Parameters
Date_
20090326
Time
20.50
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
45.3
DW
83.400 usec
DE
6.50 usec
TE
298.7 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
4.118
4.087
4.076
4.024
4.017
4.013
3.999
3.992
4.270
4.258
4.239
4.226
7.259
5.903
5.882
5.462
5.438
5.418
5.398
5.374
5.251
5.227
5.204
4.737
4.270
4.258
4.239
4.226
4.118
4.087
4.076
4.024
4.017
4.013
3.999
3.992
3.423
2.021
2.017
1.981
1.818
5.462
5.438
5.418
5.398
5.374
5.251
5.227
5.204
5.903
5.882
7.843
S64
4.2
4.1
4.0
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300095 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
3
2
6.095
3.103
3.098
4
1.027
5
1.071
1.067
1.031
6
2.094
7
2.044
1.021
8
1.073
9
1.000
10
1
1D NMR plot parameters
20.00
CY
10.50
F1P
6.065
F1
2426.88
ppm CX
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
prp-alcohol-sug
EXPNO
1
PROCNO
1
20.59
20.47
20.43
20.10
85.61
77.32
77.00
76.68
74.96
72.58
70.30
67.65
61.50
56.27
120.19
148.50
170.50
169.89
169.36
169.05
S65
F2 - Acquisition Parameters
Date_
20100107
Time
21.48
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
207
DS
0
SWH
25062.656 Hz
FIDRES
0.382426 Hz
AQ
1.3074932 sec
RG
4096
DW
19.950 usec
DE
6.50 usec
TE
297.1 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6243390 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
100.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127528 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
5.8 ppm
5.4
5.3
5.2
5.1
5.0
4.9
4.1
4.0
ppm
3.75
4.769
4.2
4.801
4.884
4.3
4.994
4.973
4.970
4.950
4.916
4.4
5.102
5.078
5.054
5.255
5.230
5.207
5.194
5.171
5.147
5.422
5.415
5.407
5.399
5.393
5.871
5.849
4.5
3.762
3.756
3.751
3.745
3.737
3.731
3.727
3.720
4.543
4.523
4.313
4.300
4.294
4.282
4.268
4.263
4.252
4.192
4.186
4.161
4.155
4.140
4.136
4.109
4.104
4.083
4.024
4.019
4.012
4.007
3.998
3.994
3.986
7.803
7.260
5.871
5.849
5.422
5.415
5.407
5.399
5.393
5.255
5.230
5.171
5.147
5.102
5.078
5.054
4.994
4.973
4.970
4.950
4.916
4.884
4.801
4.769
4.543
4.523
4.313
4.300
4.294
4.282
4.268
4.263
4.252
4.192
4.186
4.161
4.140
4.136
4.109
4.104
2.095
2.056
2.048
2.016
1.998
1.960
1.941
1.875
0.041
S66
4.8
ppm
Current Data Parameters
NAME
prp-triaz
EXPNO
1
PROCNO
1
F2 - Acquisition Parameters
Date_
20100428
Time
16.36
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zg30
TD
16384
SOLVENT
CDCl3
NS
16
DS
0
SWH
5995.204 Hz
FIDRES
0.365918 Hz
AQ
1.3664756 sec
RG
22
DW
83.400 usec
DE
8.00 usec
TE
673.2 K
D1
1.50000000 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
1H
P1
10.00 usec
PL1
0.00 dB
SFO1
400.1326008 MHz
ppm
F2 - Processing parameters
SI
16384
SF
400.1300091 MHz
WDW
EM
SSB
0
LB
0.10 Hz
GB
0
PC
1.00
7
6
5
4
3
2
1
3.029
3.046
3.029
3.036
3.093
3.070
3.003
3.053
8
1.055
2.032
1.088
1.097
1.042
1.075
1.002
1.049
1.032
2.054
2.014
1.040
1.090
9
1.000
10
1D NMR plot parameters
20.00
12.80
F1P
2.164
F1
865.96
ppm CX
CY
cm
cm
ppm
Hz
Electronic Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2011
Current Data Parameters
NAME
prp-triaz
EXPNO
2
PROCNO
1
0.94
20.70
20.58
20.52
20.45
20.03
98.71
85.79
77.32
77.20
77.00
76.68
75.16
72.60
72.35
71.71
71.02
70.36
68.34
67.61
61.82
61.71
61.44
121.87
144.18
170.66
170.37
170.16
169.78
169.35
169.32
169.04
S67
F2 - Acquisition Parameters
Date_
20100428
Time
16.39
INSTRUM
spect
PROBHD
5 mm BBO BB-1H
PULPROG
zgpg30
TD
65536
SOLVENT
CDCl3
NS
84
DS
0
SWH
25125.629 Hz
FIDRES
0.383387 Hz
AQ
1.3042164 sec
RG
4096
DW
19.900 usec
DE
8.00 usec
TE
673.2 K
D1
2.00000000 sec
d11
0.03000000 sec
DELTA
1.89999998 sec
MCREST
0.00000000 sec
MCWRK
0.01500000 sec
======== CHANNEL f1 ========
NUC1
13C
P1
8.90 usec
PL1
5.00 dB
SFO1
100.6243390 MHz
======== CHANNEL f2 ========
CPDPRG2
waltz16
NUC2
1H
PCPD2
90.00 usec
PL2
0.00 dB
PL12
19.10 dB
PL13
22.10 dB
SFO2
400.1319000 MHz
220
200
180
160
140
120
100
80
60
40
20
ppm
F2 - Processing parameters
SI
32768
SF
100.6127509 MHz
WDW
EM
SSB
0
LB
1.00 Hz
GB
0
PC
1.40