HIGHER-CARBON SUGARS .14. THE EFFECT OF DOUBLE-BOND GEOMETRY ON THE CRYSTALLOGRAPHIC CONFORMATIONS OF 2 ENOPYRANURONATES

被引：10
作者：
BARNES, JC
BRIMACOMBE, JS
IRVINE, DJ
机构：
[1] UNIV DUNDEE,DEPT CHEM,DUNDEE DD1 4HN,SCOTLAND
[2] UNIV ST ANDREWS,DEPT CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND
来源：
CARBOHYDRATE RESEARCH | 1990年 / 200卷
关键词：
D O I：
10.1016/0008-6215(90)84183-U
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：
In the crystal structure of methyl (Z)-8,9-dideoxy-1,2:3,4:6,7-tri-O-isopropylidene-a-d-threo-d-galacto-dec-8- enopyranuronate (10), the allylic system adopts an eclipsed conformation with the smallest group, H-7, at the adjacent stereocentre eclipsing the olefinic double bond. The allylic system of methyl (E)-6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-a-d-glycero-d-galacto-non-7-enopyranuronate (11) also adopts an eclipsed conformation in the crystal, but with the benzyloxy group at the adjacent stereocentre eclipsing the olefinic double bond. These ground-state conformations in the solid state provide some insight into the vastly different facial stereoselectivities of 10 and 11 towards catalytic osmylation. © 1990.
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页码：77 / 89
页数：13
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