Benzyl derivatives of N-2,4-dinitrophenyl-D-glucosamine and their use for oligosaccharide synthesis

Article abstract of DOI:10.1246/bcsj.73.173

Four tri-O-benzyl derivatives of 2-deoxy-2-(2,4-dinitroanilino)-D- glucopyranose were synthesized. Glycosylation using 3,4,6-tri-O-benzyl-2- deoxy-2-(2,4-dinitroanilino)-D-glucopyranose as glycosyl donor and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine produced β-glycosides with complete selectivity. Starting from benzyl 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D- glucopyranoside as acceptor, O-α-D-galactopyranosyl-(1 → 4)-O-β-D- galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-D-glucopyranose, the human blood-group P₁-antigenic determinant, was synthesized.