Synthesis of two new haptens of 16α-hydroxydehydroepiandrosterone (3β,16α-dihydroxyandrost-5-en-17-one)

Synthetic routes leading to 19 E and 7 Z O-(carboxymethyl)oximes derived from 16α-hydroxydehydroepiandrosterone were developed using two independent methods for introduction of the 16α-hydroxy group. Firstly, the oxime moiety was built, and then, either epoxidation of the enol acetate followed by th...

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Bibliographic Details
Published in:Steroids 2003-02, Vol.68 (2), p.149-158
Main Authors: Pouzar, Vladimı́r, Černý, Ivan, Lapčı́k, Oldřich, Hill, Martin, Hampl, Richard
Format: Article
Language:English
Subjects:
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Hapten
O-(carboxymethyl)oxime
Steroid
Synthesis
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Summary:Synthetic routes leading to 19 E and 7 Z O-(carboxymethyl)oximes derived from 16α-hydroxydehydroepiandrosterone were developed using two independent methods for introduction of the 16α-hydroxy group. Firstly, the oxime moiety was built, and then, either epoxidation of the enol acetate followed by the boron trifluoride mediated rearrangement or alkaline hydrolysis of the corresponding α-bromide in aqueous N, N-dimethylformamide were employed. The last step in both methods was removal of the protecting groups, which consisted of acid deprotection of the acetates and gentle alkaline hydrolysis of the methyl ester. Final haptens were designed as components for immunoanalytical kits.
ISSN:0039-128X
1878-5867
DOI:10.1016/S0039-128X(02)00176-9