A Stereocontrolled Construction of 2-Deoxy-β-glycosidic Linkages via 1,2-trans-β-Glycosidation of 2-Deoxy-2-[(p-methoxyphenyl)thio] glycopyranosyl N,N,N′,N′-Tetramethylphosphoroamidates

A stereocontrolled synthesis of 2-deoxy-β-glycosides has been achieved by developing a salient 1,2-trans-glycosidation method with 2-deoxy-2-[(p-methoxyphenyl)thio]glycopyranosyl N,N,N′,N′-tetramethylphosphoroamidates as glycosyl donors followed by a reductive removal of the p-methoxyphenylthio group with Raney nickel. The p-methoxyphenylthio group equatorially disposed at C-2 has proven to be an excellent stereodirecting auxiliary.