Synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitors

The C-glucosyl aldehyde, 2-C-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)ethanal was prepared from the C-glucopyranosyl propene precursor by ozonolysis. Reductive amination of the C-glucosyl aldehyde and subsequent deprotection gave 1-anilino-2-C-(alpha-D-glucopyranosyl)ethane. The E and Z isomers of the oxime derivative, 1-C-(alpha-D-arabinofuranosyl)methanal oxime were prepared by treating their aldehyde precursor with hydroxylamine. Acetylation of the oxime, followed by catalytic hydrogenation and deprotection, Save the corresponding 1-C-(alpha-D-arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy-D-lyxo-furanoside. Inhibition studies with these compounds on beta-D-glucosidase from sweet almond, using o-nitrophenyl D-glucopyranoside as substrate, were carried out. (C) 1999 Elsevier Science Ltd. All rights reserved.