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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Authors: | J. M. J. Tronchet J. M. Bourgeois |
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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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