Formation of anomeric phosphodiester linkages using H-phosphonate acceptors

A new way of constructing anomeric glycosyl phosphodiester linkages has bee n explored. Non-anomeric monosaccharide hydrogen phosphonate monoesters (5 and 9) have been used as accepters in couplings using various benzylated ga lactosyl donors (trichloroacetimidate, thioglycoside, bromo and chloro suga rs, 1-4, 7 and 8) and promoters to give, after oxidation, good yields of ph osphodiester linked "disaccharides" (6 and 10), products usually obtained b y using an anomeric hydrogen monophosphonate, a hydroxyl acceptor and pival oyl chloride as coupling reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.