Synthesis of a Site-Specific Deuterium Substituted Methyl β-D-Glucan Decasaccharide

Abstract

Synthesis of a (β-D-glucan decasaccharide, with alternating (β-1,3 and (β-1,4-linkages, is described. The decasaccharide is fully C-deuterated except for the central cellobiose residue. The main glycosylation methods used were activation of glycosyl bromides with silver triflate or activation of thioglycosides with dimethyl(methylthio)sulfonium triflate (DMTST). In order to establish the anomeric configuration of the various oligosaccharide derivatives, a fully C-protonated decasaccharide was also synthesized by a parallel route.