213838-31-4Relevant academic research and scientific papers
Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases. A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes
Fuentes, Jose,Molina, Jose L.,Pradera, M. Angeles
, p. 2517 - 2532 (1998)
Reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranosyl thioamide without significant deacetylation. This thioamide in solution presents Z-anti as the sole configuration. Reactions of 5 with carbanions which have an ethoxycarbonyl group are a way to prepare anomerically pure N- nucleoside derivatives of pyrrole and tetrahydropyridine. Reactions of 5 with carbanions stabilized by one cyano group are used to prepare glucosylamino thiophenes with only the β-configuration. Some other stereochemical aspects of the prepared compounds are discussed.
