Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines Original Research Article

Protected glycosyl azides react with acyl chlorides in the presence of triphenylphosphine to afford glycosylamides in high yields, at room temperature. Starting from the β-glycosyl azides, the reaction is highly stereoselective and occurs with retention of configuration, whereas the α-azido anomers display a lower stereoselectivity giving rise to α/β mixtures of glycosylamides. The reaction was applied to several monosaccharidic azides and to lactosyl azide with various acyl chlorides; it was shown to be of general use for preparing 1,2-trans β-glycosylamides.