C-GLYCOFURANOSIDES VIA TANDEM WITTIG-MICHAEL SEQUENCE USING A THIAZOLE-ARMED PHOSPHORANE - A ROUTE TO C-FURANOSYL ALPHA-HYDROXY PROPANALS AND PROPIONIC ACIDS

被引：17

作者：

DONDONI, A

MARRA, A

机构：

[1] Dipartimento di Chimica, Laboratorio di Chimica Organica, Universitá, Ferrara

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 45期

关键词：

C-GLYCOSIDES; SUGAR HYDROXY ALDEHYDES; SUGAR HYDROXY ACIDS; 2-THIAZOLYLCARBONYLMETHYLENETRIPHENYLPHOSPHORANE; C-GLYCOSIDATION;

D O I：

10.1016/S0040-4039(00)79321-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of alpha- and beta-1-C-(2-thiazolacyl)-glycosides (66 - 93 % overall yield). The beta-linked C-glycoside derived from 2,3:5,6-di-O-isopropylidene-D-mannofuranose was reduced to (R) and (S) alcohols which after protection as O-benzyl ethers were transformed to alpha-alkoxy aldehydes by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding alpha-alkoxy acids.

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页码：7327 / 7330

页数：4

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