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

Four tri-O-benzyl derivatives of 2-deoxy-2-(2,4-dinitroanilino)-D-glucopyra nose 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 o f p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and tr iethylamine produced beta-glycosides with complete selectivity. Starting fr om benzyl 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroaniliano)-beta-D-glucopyran oside as acceptor, O-alpha-D-galactopyranosyl-(1-->4)-O-beta-D-galactopyran osyl-(1-->4)-2-acetamido-2-deoxy-D-glucopyranose, the human blood-group P-1 -antigenic determinant, was synthesized.