REACTIONS OF PER-O-ACETYLGLUCOSYL ISOTHIOCYANATE WITH CARBON BASES - A NEW METHOD FOR THE STEREOCONTROLLED SYNTHESES OF NUCLEOSIDES AND GLUCOSYLAMINOTHIOPHENES

Reaction of tetra-O-acetyl-beta-D-glucopyranosylisothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranos yl thioamide without significant deacetylation. This thioamide in solu tion presents Z-anti as the sole configuration. Reactions of 5 with ca rbanions which have an ethoxycarbonyl group are a way to prepare anome rically pure N-nucleoside derivatives of pyrrole and tetrahydropyridin e. Reactions of 5 with carbanions stabilized by one cyano group are us ed to prepare glucosylamino thiophenes with only the B-configuration. Some other stereochemical aspects of the prepared compounds are discus sed. (C) 1998 Elsevier Science Ltd. All rights reserved.