SYNTHESIS OF METHYL (ETHYL 2-O-ACYL-3,4-DI-O-BENZYL-1-THIO-BETA-D-GLUCOPYRANOSID)URONATES AND EVALUATION OF THEIR USE AS REACTIVE BETA-SELECTIVE GLUCURONIC-ACID DONORS

被引:82
作者
GAREGG, PJ [1 ]
OLSSON, L [1 ]
OSCARSON, S [1 ]
机构
[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN
关键词
D O I
10.1021/jo00112a046
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of derivatives of methyl (ethyl 2-0-acyl-3,4-di-O-benzyl-1-thio-beta-D-glucopyranosid)-uronate with different ester groups (acetyl, benzoyl, pivaloyl, and anisoyl) at O-2 is described. The synthesis proceeds via a two-step oxidation (DMSO/DCC followed by PDC/MeOH) of C-6 on a suitably protected glucose derivative to give directly the methyl glucuronic ester without affecting the thioglycoside. The thioglucuronides were tested as donors in coupling reactions with unreactive carbohydrate alcohols using dimethyl(methylthio)sulfonium triflate (DMTST) as promoter, Due to the activating benzyl protecting groups at O-3 and -4, the sluggishness of fully acylated glucuronic acid donors could be overcome and glucuronide disaccharides were produced in fair to good yields. The glucuronides were obtained with the desired P-configuration because of the participating group at O-2. Among the different ester groups tried, the benzoyl group was found to give the highest yield in the couplings.
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页码:2200 / 2204
页数:5
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