C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids

A Dondoni, A Marra

Index: Dondoni, Alessandro; Marra, Alberto Tetrahedron Letters, 1993 , vol. 34, # 45 p. 7327 - 7330

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Citation Number: 16

Abstract

Abstract The reactions of 2-thiazolylcarbonylmethylenetriphenylphosph... with five protected D-furanoses (manno, ribo, arabino, xylo, and lyxo) in refluxing toluene lead to mixtures of α- and β-1-C-(2-thiazolacyl)-glycosides (66–93% overall yield). The β-linked C-glycosides derived from 2, 3: 5, 6-di-O-isopropylidene-D-mannnofuranose was reduced to (R) and (S) akohols which after protection as O-benzyl ethers were transformed to α-alkoxy aldehydes ...