Abstract

Glycosidation reactions of 5-thioxylopyranosides were examined. The reaction of a 1,5-dithioxyloside derivative with N-iodosuccinimide and trifluoromethanesulfonate gave ring-opened products, but no glycosylated products. On the other hand, a 5-thioxylopyranosyl trichloroacetimidate derivative was found to react with aliphatic alcohols and a sugar alcohol to give a 5-thio analog of biologically important β(1,4)xylopyranoside structures.

Keywords: Thiosugar, thioglycoside, glycosyl donor, 5-thioxylopyranose, glycosidation