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The allyl group for protection in carbohydrate chemistry part 19. the coupling of allyl 2 3 di o methyl 4 o 3 6 di o methyl beta d glucopyranosyl alpha l rhamnopyranoside to bovine serum albumin preparation of a diagnostic reagent for antibodies to the major glycolipid of mycobacterium leprae the leprosy bacillus in the human sera



The allyl group for protection in carbohydrate chemistry part 19. the coupling of allyl 2 3 di o methyl 4 o 3 6 di o methyl beta d glucopyranosyl alpha l rhamnopyranoside to bovine serum albumin preparation of a diagnostic reagent for antibodies to the major glycolipid of mycobacterium leprae the leprosy bacillus in the human sera



Journal of the Chemical Society Perkin Transactions I (5): 1165-1170



Epoxidation of allyl 4-O-(2,4-di-O-benzyl-3,6-di-O-methyl-.beta.-D-glucopyranosyl)-2,3-di-O-methyl-.alpha.-L-rhamnopyranoside and subsequent alkaline hydrolysis of the epoxide and hydrogenolysis of the benzyl groups gave 2', 3'-dihydroxypropyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-.beta.-D-glucopyranosyl)-.alpha.-L-rhamnopyranoside which was cleaved with sodium metaperiodate to give the corresponding formylmethyl glycoside. Two other routes to the latter compound, via allyl 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-.beta.-D-glucopyranosyl)-.alpha.-L-rhamnopyranoside, were also developed. The formylmethyl glycoside was coupled to bovine serum albumin using 'reductive amination' in the presence of sodium cyanoborohydride to give a glycoconjugate useful for the serodiagnosis of antibodies to the major glycolipid of Mycobacterium leprae in the sera of leprosy patients. 5',6'-Dihydroxyhexyl and 10',11'-dihydroxyundecyl 3,6-di-O-methyl-.beta.-D-glucopyranosides were also prepared as intermediates for the synthesis of the 4-formylbutyl and 9-formylnonyl glucosides respectively which are also suitable for coupling to bovine serum albumin by the 'reductive amination' technique.

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