A Convenient Synthesis of S-Glycosyl Donors of D-Glucose and O-Glycosylations Involving the New Reagent

Abstract

The synthesis of S-glycosyl donors from 2, 3, 4, 6-tetra-O-benzyl-α-glucopyranose (1) using S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (2) was carried out by a one-step reaction. One of the S-glycosyl donors, S-1-(1'-phenyl-1H-tetrazolyl)2, 3, 4, 6-tetra-O-benzyl-β-D-glucopyranose (3a), was utilized for glycosylation of glycosyl acceptors such as methanol or cholesterol using silver triflate as a promoter.