Acrylate Side Chain Derivatives of 5β-Steroids

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Title:Acrylate Side Chain Derivatives of 5β-Steroids
Creators:
Pouzar, Vladimír
Černý, Ivan
Drašar, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 12, pp. 2963-2976

Abstract

Steroids with 5β-configuration and acrylate 17β-side chain, namely (20<i>E</i>)-3β-hydroxy-5β-pregnane-21-carboxylate (<i>XVI</i>), its 3α-epimer <i>XXVI</i>, and homological ethyl ester <i>XVIII</i> were prepared from 3β-(2-tetrahydropyranyloxy)-21-norpregn-5-en-20-ol (<i>I</i>). The stereoselectivity of key steps was checked. Whereas hydrogenation of 4-en-3-one derivative <i>IV</i> gave exclusively 5β-derivative <i>VI</i>, the subsequent borohydride reduction yielded 3β- and 3α-hydroxy derivatives <i>VII</i> and <i>XI</i> in 1 : 4 ratio. The 3-hydroxy derivatives prepared (<i>XVI, XVIII</i>, and <i>XXVI</i>) were converted to the corresponding hemisuccinates (<i>XX</i> and <i>XXVIII</i>) and β-D-glucopyranosides (<i>XXII, XVIV</i>, and <i>XXX</i>) for latter use in biological studies.

Title:Acrylate Side Chain Derivatives of 5β-Steroids
Creators:
Pouzar, Vladimír
Černý, Ivan
Drašar, Pavel
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:58
Number:12
Page Range:pp. 2963-2976
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19932963UNSPECIFIED
ID Code:410
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:00

Citation

Pouzar, Vladimír; Černý, Ivan; Drašar, Pavel (1993) Acrylate Side Chain Derivatives of 5β-Steroids. Collection of Czechoslovak Chemical Communications, 58 (12). pp. 2963-2976. ISSN 0010-0765

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