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The allyl group for protection in carbohydrate chemistry 14. synthesis of 2 3 di o methyl 4 o 3 6 di o methyl beta d glucopyranosyl l rhamnopyranose and its alpha propyl glycoside a haptenic portion of the major glycolipid from mycobacterium leprae



The allyl group for protection in carbohydrate chemistry 14. synthesis of 2 3 di o methyl 4 o 3 6 di o methyl beta d glucopyranosyl l rhamnopyranose and its alpha propyl glycoside a haptenic portion of the major glycolipid from mycobacterium leprae



Journal of Carbohydrate Chemistry 2(3): 207-224



3,6-Di-O-methyl-D-glucose was prepared via 5-O-allyl-1,2-O-isopropylidene-3-O-methyl-.alpha.-D-glucofuranose and was converted into 2,4-di-O-acetyl-3,6-di-O-methyl-D-glucopyranosyl chloride. Condensation of the chlorosugar with methanol or allyl 2,3-O-isopropylidene-.alpha.-L-rhamnopyranoside gave the corresponding crystalline .beta.-glycosides. The allyl 4-O-(2,4-di-O-acetyl-3,6-di-O-methyl-.beta.-D-glucopyranosyl)-2,3-O-isopropylidene-.alpha.-L-rhamnopyranoside was converted into the title compounds and into crystalline 2,3-di-O-acetyl-4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-.beta.-D-glucopyranosyl)-L-rhamnopyranosyl chloride which should serve as an intermediate for the synthesis of the trisaccharide portion of the major glycolipid of M. leprae.

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