Abstract
A crystalline mixed ester, 6- O-acetyl-2,3,4-tri- O-[(+)-3-methylvaleryl]-β- d-glucopyranose, was obtained from Turkish tobacco by column chromatography and liquid-liquid partitions of a hexane extract. Saponification of the ester gave glucose, identified by paper chromatography, and acetic and 3-methylpentanoic (3-methylvaleric) acids, identified by gas chromatography and by the formation of their p-phenylphenacyl esters. Exhaustive methylation of the mixed ester, followed by saponification of the methylated ester gave methyl β- d-glucopyranoside. Confirmation of the structure of the ester was provided by its synthesis from d-glucose, (+)-3-methylvaleric acid, and acidic acid in 43% yield.
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