C-GLYCOSYL COMPOUNDS .24. REACTION OF ORGANOCUPRATE REAGENTS WITH PROTECTED 1,2-ANHYDRO SUGARS - STEREOCONTROLLED SYNTHESIS OF 2-DEOXY-C-GLYCOSYL COMPOUNDS

被引:13
作者
BELLOSTA, V
CZERNECKI, S
机构
[1] UNIV PARIS 06,CHIM GLUCIDES LAB,TOUR 74,4 PL JUSSIEU,F-75230 PARIS 05,FRANCE
[2] ESPCI,RECH ORGAN LAB,CNRS,UA 476,F-75005 PARIS,FRANCE
关键词
D O I
10.1016/0008-6215(83)85007-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The reaction of protected 1,2-anhydro-alpha-D-gluco- and beta-D-manno-pyranoses with alkyl and phenyl organocuprates afforded the corresponding C-glycosyl compounds in acceptable to high yield. Complete stereocontrol was obtained, leading respectively to the beta-D or the alpha-D anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-alpha-D-C-glycosyl compounds.
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页码:275 / 284
页数:10
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