Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime

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Title:Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime
Creators:
Fajkoš, Jan
Pouzar, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 12, pp. 2884-2891

Abstract

The title compound <i>IX</i> was synthesized from triol diester <i>I</i>. Catalytic hydrogenation over Adams’ catalyst afforded the 5α and 5β isomers <i>II</i> and <i>III</i> which were oxidized under mild conditions to the aldehydes <i>IV</i> and <i>XII</i>. Reaction with (O-carboxymethyl)hydroxylamine hemihydrochloride followed by methylation with diazomethane gave the oximes <i>VIII</i> and <i>XIV</i>. Partial hydrolysis to the alcohols <i>VI</i> and <i>XIII</i> and Jones’ oxidation yielded the 3-oxo derivatives <i>XI</i> and <i>XVI</i>. Complete hydrolysis of the diester <i>XI</i> afforded the desired hapten <i>IX</i>.

Title:Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime
Creators:
Fajkoš, Jan
Pouzar, Vladimír
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. 2884-2891
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912884UNSPECIFIED
ID Code:5195
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:33

Citation

Fajkoš, Jan; Pouzar, Vladimír (1991) Synthesis of (19E)-17β-hydroxy-3-oxo-5α-androstan-19-al 19-(O-carboxymethyl)oxime. Collection of Czechoslovak Chemical Communications, 56 (12). pp. 2884-2891. ISSN 0010-0765

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