SYNTHESIS OF 4 DIASTEREOMERIC OCTOFURANOSES FROM D-GLUCOFURANURONO-6,3-LACTONE VIA GRIGNARD REACTIONS

被引:10
作者
DAX, K
FECHTER, M
GRADNIG, G
GRASSBERGER, V
ILLASZEWICZ, C
UNGERANK, M
STUTZ, AE
机构
[1] Institut für Organische Chemie, Technische Universität Graz, A-8010 Graz
关键词
D O I
10.1016/0008-6215(91)84117-W
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
Reduction of 5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-alpha-D-gluco- (2) and -beta-L-idofuranurono-6,3-lactone (3) with diisobutylaluminum hydride (DIBAL-H) to the respective hemiacetal at C-6, followed by reaction with vinylmagnesium bromide in either ether or tetrahydrofuran, gives the corresponding diastereomeric pairs of 7,8-dideoxyoct-7-eno-1,4-furanoses. The configurations of the products at C-6 were determined after oxidative cleavage of the terminal double bond and reduction of the aldehyde by conversion of the resulting heptoses into the known corresponding per-O-acetylated heptitols.
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页码:59 / 70
页数:12
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