Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors

RJ Williams, CE Paul, M Nitz

Index: Williams, Rohan J.; Paul, Caroline E.; Nitz, Mark Carbohydrate Research, 2014 , vol. 386, # 1 p. 73 - 77

Full Text: HTML

Citation Number: 10

Abstract

Abstract A range of N′-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting-group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In ...