Utilisation d'ylides du phosphore non stabilisés en chimie des sucres VI. Sucres ramifiés dérivés des di‐O‐isopropylidène‐1,2:5,6‐α‐D‐ribo‐et‐α‐D‐xylo‐hexofurannosul‐3‐oses

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Abstract
The cis and trans isomers of 3‐deoxy‐1,2:5,6‐di‐O‐isopropylidene‐3‐C‐methylthiomethylene‐α‐D‐xylo‐ and ‐α‐D‐ribo‐hexofuranoses have been prepared by treatment of 1,2:5,6‐di‐O‐isopropylidene‐α‐D‐xylo‐ and ‐α‐D‐ribo‐hexofuran‐3‐uloses with methylthiomethylene‐triphenylphosphorane. Configurations are assigned by NMR. A new type of 4J is described. Hydrogenation‐desulfurization of the methylthiovinylic sugars affords 3‐deoxy‐3‐methyl sugars of the D‐allo, D‐gulo, and D‐galacto series. Derivatives of 3‐deoxy‐3‐methyl‐D‐lyxose and 3‐deoxy‐3‐methyl‐D‐ribose are prepared by chain‐shortening of derivatives of the corresponding 3‐deoxy‐3‐methyl‐hexoses.

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