Studies on Glycosidase Inhibitors : Synthesis of 2, 6-Dideoxy-2, 6-imino-L-gulonic Acid and Its 3-Deoxy Analog

Abstract

2, 6-Dideoxy-2, 6-imino-L-gulonic acid (1) with inhibitory activity against β-D-glucuronidase and α-L-iduronidase was stereoselectively synthesized from 2, 3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1, 5-dideoxy-1, 5-imino-D-glucitol (4). Through a deoxygenation reaction at the C-4 position of the latter, 2, 3, 6-trideoxy-2, 6-imino-L-gulonic acid (2) was also prepared.