153941-94-7Relevant academic research and scientific papers
C-glycofuranosides via tandem Wittig-Michael sequence using a thiazole-armed phosphorane. A route to C-furanosyl α-hydroxy propanals and propionic acids
Dondoni, Alessandro,Marra, Alberto
, p. 7327 - 7330 (2007/10/02)
The reactions of 2-thiazolylcarbonylmethylenetriphenylphosphorane 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 by thiazole-to-formyl conversion; the aldehydes were oxidized to the corresponding α-alkoxy acids.
