Facile synthesis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli 19ab
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Carbohydrate Research p. 8 - 12 (2012)
Update date: 2022-07-29
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Article abstract of DOI:10.1016/j.carres.2012.09.005
A straightforward synthesis of the pentasaccharide with all α-linked glycosyl linkages corresponding to the cell wall O-antigen of Escherichia coli 19ab has been achieved in excellent yield using sequential glycosylations of monosaccharide intermediates. The structure of the target compound and its synthetic intermediates were unambiguously characterized using their spectral analysis. A generalized glycosylation condition has been used in all glycosylations and minimum number of protecting group manipulations were involved during the synthesis of the target compound.
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Full text of DOI:10.1016/j.carres.2012.09.005
Supporting Information
Facile synthesis of the pentasaccharide repeating unit of the cell wall O -
antigen of Escherichia coli 19ab
Tamashree Ghosh and Anup Kumar Misra*
Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M,
Kolkata-700054, India
Index
Subject
Page No.
2-33
1D and 2D NMR spectra of compounds 6-12 and 1
1
1 H NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (6).
2
CCl 4
13 C NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (6).
3
1 H NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-rhamnopyranosyl)-
(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (7).
4
CCl 4
13 C NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-rhamnopyranosyl)-
(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (7).
5
2 D 1 H- 1 H COSY NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (7) (expanded
region).
6
CCl 4
2 D 1 H- 13 C HSQC NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamnopyranoside (7) (expanded
region).
7
1 H NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (8).
8
CCl 4
13 C NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (8).
9
2D 1 H- 1 H COSY NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -
benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-
(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (8) (expanded region).
10
CCl 4
2D 1 H- 13 C HSQC NMR spectrum of p -methoxyphenyl (2- O -acetyl-3,4-di- O -
benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-
(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (8) (expanded region).
11
1 H NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (9).
12
CCl 4
13 C NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (9).
13
2D 1 H- 1 H COSY NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (9) (expanded region).
14
CCl 4
2D 1 H- 13 C HSQC NMR spectrum of p -methoxyphenyl (3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (9) (expanded region).
15
1 H NMR spectrum of p -methoxyphenyl (2- O -acetyl-2-azido-4,6- O -
benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (10) .
16
13 C NMR spectrum of p -methoxyphenyl (2- O -acetyl-2-azido-4,6- O -
benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (10).
17
13 C DEPT 135 NMR spectrum of p -methoxyphenyl (2- O -acetyl-2-azido-4,6- O -
benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (10) .
18
2D 1 H- 1 H COSY NMR spectrum of p -methoxyphenyl (2- O -acetyl-2-azido-4,6-
O -benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (10) (expanded region).
19
2D 1 H- 13 C HSQC NMR spectrum of p -methoxyphenyl (2- O -acetyl-2-azido-4,6-
O -benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (10) (expanded region).
20
1 H NMR spectrum of p -methoxyphenyl (2-azido-4,6- O -benzylidene-2-deoxy-
-D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-
(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-
rhamanopyranoside (11) .
21
13 C NMR spectrum of p -methoxyphenyl (2-azido-4,6- O -benzylidene-2-deoxy-
-D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-
(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-
rhamanopyranoside (11) .
22
2D 1 H- 1 H COSY NMR spectrum of p -methoxyphenyl (2-azido-4,6- O -
benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (11) (expanded region).
23
2D 1 H- 13 C HSQC NMR spectrum of p -methoxyphenyl (2-azido-4,6- O -
benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-3,4-
di- O -benzyl- -L-rhamanopyranoside (11) (expanded region).
24
1 H NMR spectrum of p -methoxyphenyl (2,3,4,6-tetra- O -benzyl- -D-glucopyranosyl)-
(1 3)-(2-azido-4,6- O -benzylidene-2-deoxy- -D-glucopyranosyl)-(1 2)-(3,4-di- O -
benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-
25
(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (12).
13 C NMR spectrum of p -methoxyphenyl (2,3,4,6-tetra- O -benzyl- -D-
glucopyranosyl)-(1 3)-(2-azido-4,6- O -benzylidene-2-deoxy- -D-glucopyranosyl)-
(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
26
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (12).
13 C DEPT 135 NMR spectrum of p -methoxyphenyl (2,3,4,6-tetra- O -benzyl- -D-
glucopyranosyl)-(1 3)-(2-azido-4,6- O -benzylidene-2-deoxy- -D-glucopyranosyl)-
(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
27
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (12).
1 H- 1 H 2D COSY NMR spectrum of p -methoxyphenyl (2,3,4,6-tetra- O -benzyl- -D-
glucopyranosyl)-(1 3)-(2-azido-4,6- O -benzylidene-2-deoxy- -D-glucopyranosyl)-
(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (12) (expanded
28
region).
1 H- 13 C 2D HSQC NMR spectrum of p -methoxyphenyl (2,3,4,6-tetra- O -benzyl- -D-
glucopyranosyl)-(1 3)-(2-azido-4,6- O -benzylidene-2-deoxy- -D-glucopyranosyl)-
(1 2)-(3,4-di- O -benzyl- -L-rhamnopyranosyl)-(1 2)-(3,4-di- O -benzyl- -L-
rhamnopyranosyl)-(1 2)-3,4-di- O -benzyl- -L-rhamanopyranoside (12) (expanded
29
region).
HOD
1 H NMR spectrum of p -methoxyphenyl ( -D-glucopyranosyl)-(1 3)-(2-acetamido-2-
deoxy- -D-glucopyranosyl)-(1 2)-( -L-rhamnopyranosyl)-(1 2)-( -L-
30
rhamnopyranosyl)-(1 2)- -L-rhamanopyranoside (1).
Ghosh, Tamashree
