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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

✍ Scribed by J. M. J. Tronchet; J. M. Bourgeois

Publisher
John Wiley and Sons
Year
1970
Tongue
German
Weight
979 KB
Volume
53
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 ^4^J 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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