PREPARATION AND CRYSTAL AND MOLECULAR-STRUCTURE OF 6-O-[(2S)-2,3-EPOXYPROPYL]-1,2/3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTOPYRANOSE - PYRANOID RING CONFORMATION IN 1,2/3,4-DI-O-ISOPROPYLIDENE-GALACTOPYRANOSE AND RELATED SYSTEMS

被引：34
|
作者：
KOLL, P [1 ]
SAAK, W [1 ]
POHL, S [1 ]
STEINER, B [1 ]
KOOS, M [1 ]
机构：
[1] SLOVAK ACAD SCI,INST CHEM,BRATISLAVA 84238,SLOVAKIA
来源：
CARBOHYDRATE RESEARCH | 1994年 / 265卷 / 02期
关键词：
PYRANOSES; CONFORMATION; X-RAY STRUCTURE; NOMENCLATURE;
D O I：
10.1016/0008-6215(94)00232-0
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 title compound was isolated by several recrystallisations from a 1:1 mixture of diastereomers which was obtained in 75% yield from the reaction of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with epichlorohydrin. The absolute configuration of this isomer (30% yield) was established by X-ray crystallography. The conformation of the pyranoid ring in this compound is compared to those in related situations. In all these cases the pyranoid ring adopts a heavily distorted conformation which is described on average as between the screw-boat S-O(5) and the twist-boat (''skew''-boat) T-O(2) with deviations in the direction of the boat B-2,B-5 in most cases. The puckering parameters for all such reported pyranoid rings were calculated or recalculated, and are given within expanded conventions of carbohydrate nomenclature.
引用
收藏
页码：237 / 248
页数：12
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