Synthesis of L-glycero-D-manno-heptopyranose-containing oligosaccharide structures found in lipopolysaccharides from Haemophilus influenzae

Article abstract of DOI:10.1016/S0008-6215(96)00275-3

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1 → 2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1 → 2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1 → 3)-L-glycero-α-D-manno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-α-D-manno-heptopyranosyl)-(1 → 2)-O-(L-glycero-α-D-manno-heptopyranosyl)-(1 → 3)-L-glycero-α-D-manno-heptopyranoside (17), 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-glucopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyl)-(1 → 4)-L-glycero-α-D-manno-heptopyranoside (5), and 2-(4-trifluoroacetamidophenyl)ethyl O-(β-D-galactopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyl)-(1 → 4)-L-glycero-α-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae.