A mild and general method for preparation of alpha-glycosyl chlorides

Abstract

A mild and efficient chlorination method for production of glycosyl chlorides is first described which employs inexpensive trichlorotriazine (TCT) and DMF as a chlorination reagent and is compatible with typical acid-labile hydroxyl protecting functions. The scope and limitations, reaction mechanism and its application in the sequential glycosylations are discussed. (C) 2009 Elsevier Ltd. All rights reserved.