An Attempt at the Direct Construction of 2-Deoxy-β-glycosidic Linkages Capitalizing on 2-Deoxyglycopyranosyl Diethyl Phosphites as Glycosyl Donors

Abstract

A direct method for the construction of 2-deoxy-β-glycosidic linkages has been developed by using 2-deoxyglycopyranosyl diethyl phosphites without neighboring group substituents at C-2 as glycosyl donors in the presence of a catalytic amount of trimethylsilyl triflate (TMSOTf), wherein glycosidations of 2-deoxy-D-gluco- and 2-deoxy-L-rhamnopyranosyl donors with primary alcohols have been found to exhibit the highest β-selectivity known to date.