Glycosylated derivatives of substituted hydroxylamine. II. The phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine

The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis acids resulted in alkyl-O-glucosaminides with the 1,2-trans-configuration of the glycoside bond. Other glucosaminides of substituted hydroxylamine were shown not to react under these conditions. The structures of the synthesized glucosaminides were confirmed by ¹H NMR spectroscopy and comparison with the authentic compounds.