Low-Concentration 1,2-trans beta-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis

Abstract

This study develops an operationally easy, efficient, and general 1,2-trans beta-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent beta-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosylsubstrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans beta-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans beta-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant beta-(1 -> 6)-glucan trisaccharide, beta-linked Gb(3) and isoGb(3) derivatives.