Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain

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Title:Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain
Creators:
Pouzar, Vladimír
Chodounská, Hana
Černý, Ivan
Drašar, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 12, pp. 2906-2916

Abstract

Aldehydes <i>II - III</i> were reacted with diethyl cyanomethylphosphonate and sodium hydride in 1,2-dimethoxyethane to give the respective pairs of unsaturated nitriles <i>IVa</i> and <i>Va, VIa</i> and <i>VIIa</i>, and <i>VIIIa</i> and <i>IXa</i> differing in configuration at the 20(21)-double bond. The pure isomers were obtained by chromatography on alumina, and the configuration at the double bond in them has been established on the basis of the coupling constants <i>J</i>(20, 21) in their <sup>1</sup>H NMR spectra. Nitriles <i>IVa - VIIa</i> and <i>IXa</i> were converted via the corresponding hydroxy derivatives into hemisuccinates <i>IVd - VIId</i> and <i>IXd</i>, and into β-D-glucosides <i>IVe - VIIe</i> and <i>IXe</i>.

Title:Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain
Creators:
Pouzar, Vladimír
Chodounská, Hana
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:56
Number:12
Page Range:pp. 2906-2916
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912906UNSPECIFIED
ID Code:5197
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:33

Citation

Pouzar, Vladimír; Chodounská, Hana; Černý, Ivan; Drašar, Pavel (1991) Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain. Collection of Czechoslovak Chemical Communications, 56 (12). pp. 2906-2916. ISSN 0010-0765

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