Carbohydrate research p. 63 - 90 (1986)
Update date:2022-08-02
Topics:
Paulsen
Lorentzen
In the presence of silver silicate, the reaction of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranosyl bromide with 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranose gave beta-glycosidically linked 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(3,4,6- tri-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)-beta-D- glucopyranose. After deacetylation and catalytic oxidation with oxygen and platinum, 1,6-anhydro-2-azido-4-O-[(2-azido-2-deoxy-beta-D-mannopyranosyl) uronic acid]-3-O-benzyl-2-deoxy-beta-D-glucopyranose was obtained. A series of intermediate steps led to the glycosyl donor 6-O-acetyl-2-azido-3-O-benzyl-4-O-[benzyl (3,4-di-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)uronate]-2-deoxy- alpha, beta-glucopyranosyl chloride which was coupled with 8-methoxycarbonyloctyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-galactopyranoside to give 8-methoxycarbonyloctyl O-[benzyl (3,4-di-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)uronate]- (1----4)-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-alpha-D-glucopyranosyl )-(1----3)-4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-galactopyranoside. Deblocking gave the spacer-linked repeating unit of the enterobacterial common antigen, beta-D-ManpNAcA-(1----4)-alpha-D-GlcpNAc-(1----3)-alpha- D-Fucp4NACO(CH2)8CO2CH3.
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Doi:10.1016/j.tet.2008.10.001
(2008)Doi:10.1016/S0040-4039(00)85162-X
(1986)Doi:10.1039/DT9870000155
(1987)Doi:10.1016/S0040-4039(00)80073-8
(1988)Doi:10.1016/0022-328X(86)80218-2
(1986)Doi:10.1246/bcsj.68.2669
(1995)