Glycosylation using 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose, -galactose, and -mannose with the aid of p-nitrobenzenesulfonyl chloride silver trifluoromethanesulfonate triethylamine system

This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl-2-de oxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6-tri- O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, sil ver trifluoromethanesulfonate, and triethylamine, and its modifications. O- (2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-alpha-D-mannopyranosy l-(1-->4)-alpha-D-mannopyranose, the repeating unit of the main chain of th e O-specific cell wall polysaccharide of E. coli O58 was synthesized.