Synthetic approach to 5 alpha-pregnanolone 19-[O-(carboxymethyl)oxime] derivatives
Syntheses of 5alpha-pregnanolone derivatives (3-hydroxy-5alpha-pregnan-20-ones) with 3alpha- and 3beta-configuration and 19-[O-(carboxymethyl)oxime] group were developed, starting from 19-hydroxy-20-oxopregn-5-en-3beta-yl acetate. After catalytic hydrogenation, acetylation and ketone protection, the...
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Published in | Collection of Czechoslovak chemical communications Vol. 69; no. 9; pp. 1805 - 1817 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
PRAGUE 6
Inst Organic Chem And Biochem
01.01.2004
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Subjects | |
Online Access | Get more information |
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Summary: | Syntheses of 5alpha-pregnanolone derivatives (3-hydroxy-5alpha-pregnan-20-ones) with 3alpha- and 3beta-configuration and 19-[O-(carboxymethyl)oxime] group were developed, starting from 19-hydroxy-20-oxopregn-5-en-3beta-yl acetate. After catalytic hydrogenation, acetylation and ketone protection, the acetyl in position 3 was removed. To obtain the 3alpha- derivative, nitrite epimerization of the intermediate tosylate was performed before the introduction of methoxymethyl protecting group, while the 3beta-derivative was protected directly. In both series, deacetylation, oxidation to an aldehyde and O-(carboxymethyl) hydroxylamine condenzation followed. Conversion to the methyl ester, simultaneous deprotection of positions 3 and 20, and alkaline hydrolysis gave the corresponding 19-[ O-(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. |
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ISSN: | 0010-0765 |
DOI: | 10.1135/cccc20041805 |