Tetrahedron: Asymmetry

Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases. A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes

J Fuentes, JL Molina, MA Pradera

文献索引：Fuentes, Jose; Molina, Jose L.; Pradera, M. Angeles Tetrahedron Asymmetry, 1998 , vol. 9, # 14 p. 2517 - 2532

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被引用次数: 23

摘要

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 ...