Synthetic Approach to 5α-Pregnanolone 19-[O-(Carboxymethyl)oxime] Derivatives

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Title:Synthetic Approach to 5α-Pregnanolone 19-[O-(Carboxymethyl)oxime] Derivatives
Creators:
Černý, Ivan
Havlíková, Helena
Hill, Martin
Hampl, Richard
Pouzar, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 9, pp. 1805-1817
Uncontrolled Keywords:Oximes, Haptens, Neurosteroids, <i>O</i>-(Carboxymethyl)oxime, Synthesis, Steroids, Hormones

Abstract

Syntheses of 5α-pregnanolone derivatives (3-hydroxy-5α-pregnan-20-ones) with 3α- and 3β-configuration and 19-[<i>O</i>-(carboxymethyl)oxime] group were developed, starting from 19-hydroxy-20-oxopregn-5-en-3β-yl acetate. After catalytic hydrogenation, acetylation and ketone protection, the acetyl in position 3 was removed. To obtain the 3α-derivative, nitrite epimerization of the intermediate tosylate was performed before the introduction of methoxymethyl protecting group, while the 3β-derivative was protected directly. In both series, deacetylation, oxidation to an aldehyde and <i>O</i>-(carboxymethyl)hydroxylamine condenzation followed. Conversion to the methyl ester, simultaneous deprotection of positions 3 and 20, and alkaline hydrolysis gave the corresponding 19-[<i>O</i>-(carboxymethyl)oximes]. The nine- and ten-step syntheses described herein (yields 19.5 and 7.3%, respectively) gave the target compounds, designed as haptens for immunological use. <p>

Title:Synthetic Approach to 5α-Pregnanolone 19-[O-(Carboxymethyl)oxime] Derivatives
Creators:
Černý, Ivan
Havlíková, Helena
Hill, Martin
Hampl, Richard
Pouzar, Vladimír
Uncontrolled Keywords:Oximes, Haptens, Neurosteroids, <i>O</i>-(Carboxymethyl)oxime, Synthesis, Steroids, Hormones
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:69
Number:9
Page Range:pp. 1805-1817
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041805UNSPECIFIED
ID Code:2306
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Černý, Ivan; Havlíková, Helena; Hill, Martin; Hampl, Richard; Pouzar, Vladimír (2004) Synthetic Approach to 5α-Pregnanolone 19-[O-(Carboxymethyl)oxime] Derivatives. Collection of Czechoslovak Chemical Communications, 69 (9). pp. 1805-1817. ISSN 0010-0765

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