Sc(OTf)3 Efficiently Catalyzed the Glycosidation of 1-C-Alkyl-2,3,4,6-tetra- O-benzyl-α-D-glucopyranosyl Acetates with Alcohols

Abstract

Several 1-C-alkyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosides were stereoselectively synthesized in good yields by the reaction of the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-?-D-glucopyranosyl acetates with alcohols in the presence of 5 mol% Sc(OTf)3. The nature of the alkyl groups at the anomeric centers of the glycosyl donors had almost no influence on the reactivity and stereoselectivity of this glycosidation. Keywords: alkyl-glycoside, glycosidation, glycosyl acetate, ketoside, lewis acid