SYNTHESIS OF L-GLYCERO-D-MANNO-HEPTOPYRANOSE-CONTAINING OLIGOSACCHARIDE STRUCTURES FOUND IN LIPOPOLYSACCHARIDES FROM HAEMOPHILUS INFLUENZAE

摘要

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D--manno-heptopyranosyl)-(1 --> 3)-L-glycero-alpha-D-mnnno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1 --> 2)-O-(L-glycero-alpha-D-manno-heptopyranosl)-(1 --> 3)-L-glycero-alpha-D-manno-heptopyranoside(17), 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-glucopyranosyl)-(1 --> 4)-O-(beta-D-glucopyranosyl)-(1 --> 4)-L-glycero-alpha-D-manno-heptopyranoside (5), and 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1 --> 4)-O-(beta-D-glucopyranosyl)-(1 --> 4)-L-glycero-alpha-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae. (C) 1997 Elsevier Science Ltd. [References: 21]