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.