Efficient Synthesis of Methylene exo-Glycals: Another Use of Glycosylthiomethyl Chlorides

摘要

A new approach to the synthesis of methylene exo-glycals is described. Oxidation of glycosylthiolmethyl chloride (GTM-Cl) with mCPBA afforded the corresponding glyco-sylchloromethyl sulfone in almost quantitative yield, which underwent KO~tBu-induced Ramberg-Baeckhand rearrangement to furnish the desired methylene exo-glycal in excellent yield.