Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
Supplementary data
Table of Contents
Figure S1. 1H NMR spectrum of 5 in DMSO-d6
Figure S2. 1H NMR spectrum of 5 in CD3OD
Figure S3. 1H NMR spectrum of 5 in CDCl3
Figure S4. 1H NMR spectrum of 6 in CDCl3
Figure S5. 1H NMR spectrum of 9 in CD3OD
Figure S6. 1H NMR spectrum of 9 in DMSO-d6
Figure S7. 1H NMR spectrum of 10 in CD3OD
Figure S8. 1H NMR spectrum of 7 in CDCl3
Figure S9. 1H NMR spectrum of 8 in CDCl3
Figure S10. 1H NMR spectrum of 8 in CD3OD
Figure S11. 1H NMR spectrum of 8 in DMSO-d6
Figure S12. 1H NMR spectrum of 11 in CD3OD
Figure S13. 1H NMR spectrum of 12 in CD3OD
Figure S14. 1H NMR spectrum of 12 in DMSO-d6
Figure S15. 1H NMR spectrum of 15 in DMSO-d6
Figure S16. 1H NMR spectrum of 16 in CD3OD
Figure S17. 1H NMR spectra (aromatic portion) of compound 5 in different solvents
Figure S18. NOESY NMR maps of compounds 12 and 5
Figure S19. Dynamic 1H NMR experiments on glycocalixarenes 5 and 9.
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
AcO
OAc
AcO
OAc
OAc
AcO
O
O
AcO
OAc
NH
S
HN
NH
HN
O O
S
O O
5
10
9
8
7
6
5
4
3
(ppm)
Figure S1. 1 H NMR spectrum of 5 in DMSO-d6 (400 MHz, 300 K)
S2
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
AcO
OAc
AcO
OAc
OAc
AcO
O
O
AcO
OAc
NH
S
HN
NH
HN
O O
S
O O
5
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
Figure S2. 1 H NMR spectrum of 5 in CD3 OD (400 MHz, 300 K)
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S3
AcO
OAc
AcO
OAc
OAc
AcO
O
O
AcO
OAc
NH
S
HN
NH
HN
O O
S
O O
5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
(ppm)
4.0
3.5
3.0
Figure S3. 1 H NMR spectrum of 5 in CDCl 3 (400 MHz, 300 K)
2.5
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S4
OAc
AcO
AcO
OAc
OAc
AcO
O
O
AcO
OAc
NH
S
HN
NH
HN
S
O O
O O
6
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
(ppm)
4.0
3.5
3.0
Figure S4. 1 H NMR spectrum of 6 in CDCl 3 (400 MHz, 300 K)
2.5
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S5
HO
OH
HO
OH
OH
HO
O
O
HO
OH
NH
S
HN
NH
HN
S
O O
O O
9
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
2.0
Figure S5. 1 H NMR spectrum of 9 in CD3 OD (400 MHz, 300 K)
1.5
1.0
0.5
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S6
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
HO
OH
HO
OH
OH
HO
O
O
HO
OH
NH
S
HN
NH
HN
S
O O
O O
9
10
9
8
7
6
(ppm)
5
4
3
Figure S6. 1 H NMR spectrum of 9 in DMSO-d6 (400 MHz, 300 K)
S7
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
OH
HO
HO
OH
OH
HO
O
O
HO
OH
NH
S
HN
NH
HN
O O
S
O O
10
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
Figure S7. 1 H NMR spectrum of 10 in CD3 OD (400 MHz, 300 K)
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S8
AcO
AcO
AcO
OAc
AcO
OAc
OAc
OAc
O
O
AcO
O
OAc
NH
O
AcO
HN
NH
S
OAc
AcO
AcO
NH
S
OAc
OAc
S HN
NH
HN
HN
S
O O
O O
7
8
7
6
5
4
3
(ppm)
Figure S8. 1 H NMR spectrum of 7 in CDCl 3 (400 MHz, 300 K)
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S9
AcO
OAc
OAc
AcO
OAc
O
O
AcO
S
OAc
AcO
O
OAc
O
AcO
HN
NH
NH
OAc
AcO
NH
S
AcO
AcO
OAc
OAc
S
NH
HN
HN
HN
S
O O
O O
8
8
7
6
5
4
3
(ppm)
Figure S9. 1 H NMR spectrum of 8 in CDCl 3 (300 MHz, 300 K)
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S10
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
AcO
OAc
OAc
AcO
OAc
O
O
AcO
S
OAc
AcO
O
OAc
O
AcO
HN
NH
NH
OAc
AcO
NH
S
AcO
AcO
OAc
OAc
S HN
NH
HN
HN
S
O O
O O
8
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
Figure S10. 1 H NMR spectrum of 8 in CD3 OD (300 MHz, 300 K)
S11
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
AcO
OAc
OAc
AcO
OAc
O
O
AcO
S
OAc
AcO
O
OAc
O
AcO
HN
NH
NH
OAc
AcO
NH
S
AcO
AcO
OAc
OAc
S HN
NH
HN
HN
S
O O
O O
8
10
9
8
7
6
5
4
3
(ppm)
Figure S11. 1 H NMR spectrum of 8 in DMSO-d6 (300 MHz, 300 K)
S12
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
HO
HO
HO
OH
HO
OH
OH
OH
O
O
HO
O
OH
S
O
HO
HN
NH
NH
OH
S
HN
HN
NH
HN
O O
OH
HO
HO
NH
S
OH
S
O O
11
7.5
7.0
6.5
6.0
5.5
5.0
4.0
4.5
(ppm)
3.5
3.0
2.5
Figure S12. 1 H NMR spectrum of 11 in CD3 OD (400 MHz, 300 K)
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S13
HO
OH
OH
HO
OH
O
O
HO
NH
O
HO
HN
OH
S
NH
HN
HN
HN
O O
OH
HO
O
OH
NH
S
OH
HO
NH
S
HO
HO
OH
S
O O
12
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
2.0
Figure S13. 1 H NMR spectrum of 12 in CD3 OD (300 MHz, 300 K)
1.5
1.0
0.5
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S14
HO
OH
OH
HO
OH
O
O
HO
NH
O
HO
HN
OH
S
NH
HN
HN
HN
O O
OH
HO
O
OH
NH
S
OH
HO
NH
S
HO
HO
OH
S
O O
12
10
9
8
7
6
5
4
3
(ppm)
Figure S14. 1 H NMR spectrum of 12 in DMSO-d6 (400 MHz, 300 K)
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S15
OAc
AcO
AcO
OAc
OAc
AcO
O
O
AcO
OAc
O
AcO
O
OAc
OAc
AcO
O
O
AcO
OAc
NH
S
HN
NH
HN
O O
O
S
O
15
10
9
8
7
6
(ppm)
5
4
3
Figure S15. 1 H NMR spectrum of 15 in DMSO-d6 (400 MHz, 300 K)
2
1
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
S16
Supplementary material (ESI) for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2003
OH
HO
HO
OH
OH
HO
O
O
HO
OH
O
O
HO
OH
OH
HO
O
O
HO
OH
NH
S
HN
NH
HN
O O
O
S
O
16
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
(ppm)
3.5
3.0
2.5
Figure S16. 1 H NMR spectrum of 16 in CD3 OD (400 MHz, 300 K)
2.0
1.5
1.0
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S17
a
b
c
7.4
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
(ppm)
Figure S17. Aromatic portion (7.5-5.5 ppm) of the 1H NMR spectra (300 MHz, 300 K)
of compound 5 in (a) CDCl3, (b) DMSO-d6 and (c) CD3OD.
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S 18
H2
H2
exp: ec238cosy 5/1
tit: noesy (d8=0.5s)
HA
HA
HB
HB
H1
H1
ppm
ppm
5.0
3.5
4.0
5.5
4.5
6.0
5.0
6.5
5.5
7.0
6.0
6.5
7.5
7.0
8.0
7.5
8.5
8.0
9.0
8.5
9.5
9.0
9.5
9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5
ppm
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
ppm
Figure S18 Left: NOESY two-dimensional map (9.5-3.0 ppm, DMSO-d6, 300 MHz, 300 K) of compound 12. Right: NOESY two-dimensional map (10.0-4.7 ppm, DMSO-d6, 400
MHz, 300 K) of compound 5.
Supplementary material (ESI) for Organic & Biomolecular Chemistry
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S19
a
a
b
b
c
c
d
d
7.4
7.2
7.0
6.8
6.6
6.4
(ppm)
6.2
6.0
5.8
5.6
7 .4
7 .2
7 .0
6 .8
6 .6
6 .4
6 .2
6 .0
5 .8
5 .6
5 .4
5 .2
(p p m )
Figure S19. Left: 1H NMR spectra (7.5-5.5 ppm, CD3OD, 400 MHz) of compound 5 at (a) 323, (b) 298, (c) 273 and (d) 223 K. Right: 1H NMR spectra (7.5-5.0
ppm, CD3OD, 400 MHz) of compound 9 at (a) 350, (b) 298, (c) 273 and (d) 213 K.