Synthesis of the inhibitors of glycanases

2,3-Epoxypropyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside was obtained by oxidation of allyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside; deacet ylation of the former compound afforded 2,3-epoxypropylacetyl-beta-D-glucop yranoside, Analogous oxidation and deacetylation of allyl 2,3,4,6-tetra-O-a cetyl-beta-D-glucopyranosyl-(1-->4)-2,3,6-tr O-acetyl-beta-D-glucopyranosid e produced 2,3-epoxypropyl 2,3,4,6-tetra- O-acetyl-beta-D-glucopyranosyl-(1 -->4)-2,3,6-O-acetyl-beta-D-glucopyranoside and 2,3-epoxypropyl beta-D-gluc opyranosyl-(1-->4)-beta-D-glucopyranoside respectively. Structure, anomeric and absolute configuration of these substances were determined by H-1 and C-13 NMR spectroscopic methods, and mass spectrometric methods. The deacety lated epoxyalkyl beta-D-glycosides were effective as irreversible active-si te directed inhibitors of beta-glycosidase from sweet almonds.