MODIFIED BILE-ACIDS - PREPARATION OF 7-ALPHA,12-ALPHA-DIHYDROXY-3-BETA-(2-HYDROXYETHOXY)-5-BETA-CHOLANIC ACID AND 7-ALPHA,12-ALPHA-DIHYDROXY-3-ALPHA-(2-HYDROXYETHOXY)-5-BETA-CHOLANIC ACID AND THEIR BIOLOGICAL-ACTIVITY

被引：46

作者：

WESS, G

KRAMER, W

BARTMANN, W

ENHSEN, A

GLOMBIK, H

MULLNER, S

BOCK, K

DRIES, A

KLEINE, H

SCHMITT, W

机构：

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 02期

关键词：

D O I：

10.1016/0040-4039(92)88048-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology for the preparation of 7-alpha,12-alpha-dihydroxy-3-beta- (2) and 7-alpha,12-alpha-dihydroxy-3-alpha-(2-hydroxyethoxy)-5-beta-cholanic acid (3) is described. Nucleophilic displacement of the 3-mesylate of unprotected cholic acid with ethylene glycol led to the 3-beta-isomer whereas the 3-alpha-isomer was synthesized via the 7,12-diacetyl protected 3-allyl ether of methyl cholate. Only the 3-alpha-isomer 3 is recognized by the ileal bile acid transport system with affinity comparable to cholic acid.

引用

页码：195 / 198

页数：4

共 9 条

[1]

BOCCHI V, 1979, SYNTHESIS-STUTTGART, P957

[2] OLEFINS OF THE CHOLANE SERIES FROM DEOXYCHOLIC AND CHOLIC ACIDS [J].