STEREOSELECTIVE SYNTHESES OF 2,4-5,6-DI-O-ISOPROPYLIDENE-1-C-PHENYL-D-GLYCERO-D-IDO-HEXITOL AND 2,4-5,6-DI-O-ISOPROPYLIDENE-1-C-PHENYL-D-GLYCERO-D-GULO-HEXITOL FROM D-GLYCERO-D-GULO-HEPTONO-GAMMA-LACTONE - X-RAY STRUCTURE OF 1-O-ACETYL-2,4-5,6-DI-O-ISOPROPYLIDENE-1-C-PHENYL-D-GLYCERO-D-IDO-HEXITOL

被引：22

作者：

SHING, TKM ^{[1
]}

TSUI, HC ^{[1
]}

ZHOU, ZH ^{[1
]}

MAK, TCW ^{[1
]}

机构：

[1] CHINESE UNIV HONG KONG,DEPT CHEM,SHA TIN,HONG KONG

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 07期

关键词：

D O I：

10.1039/p19920000887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1-O-acetyl-derivative 12.

引用

页码：887 / 893

页数：7

共 14 条

[1]

Brimacombe J. S., 1966, CARBOHYD RES, V2, P341

[2] STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].