Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups

Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phospha te leaving group were easily prepared by the addition of the anomeric hydro xyl group of 2,3,4,6-tetra-O-benzyl-alpha,beta -D-giucopyranose to diphenyl phosphinic and propane 1.3-diyldioxyphosphoryl chlorides. These glycosyl do nors were selectively glycosylated with a number of primary and secondary o xygen nucleophiles in the presence of trimethylsilyl triflate (TMSOTf). The use of 1,3-diyl phosphate resulted in the stereoselective formation of bet a -O-linked glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.