A Facile Synthesis of Anomeric Benzyl Protected Man-Β(1,4)GlcNAc Scaffold as a Building Block for a Rapid Expansion of Oligosaccharide Molecular Diversity

Abstract

A facile and efficient strategy for accessing Man-β(1,4)GlcNAc core was investigated. Anomeric benzyl protected acceptor derived from N-glycosamine hydrochloride was glycosylated with orthogonally protected thioglycoside to afford the gluc-β(1,4)GlcNAc scaffold which was epimerized via triflation to obtain the Man-β(1,4)GlcNAc derivative. The disaccharide Man-β(1,4)GlcNAc scaffold could be used as the basic building block for the divergent synthesis of various oligosaccharide structures for detailed biological activity investigation of glycans. The compounds were characterized by NMR, MS and Infra-red (IR) spectroscopy.