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Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone
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Veröffentlicht/Copyright:
30. August 2011
Abstract
In order to develop an immunoassay of 7β-hydroxy-epiandrosterone, a stereoselective synthesis of a specific hapten, 7β-hydroxy-19-oxo-androstan 19-(O-carboxymethyl)oxime (17), was performed. This synthesis was achieved in 16% overall yield starting from the well-known 3β-acetoxy-19-hydroxy-5-androsten-17-one (1). After coupling of the alkyl oxime moiety, an allylic oxidation of the C-7 carbon under mild conditions followed by two selective reductions established all the functionalities of the final compound 17.
Keywords: anti-inflammatory compound; stereoselective synthesis; 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone
Received: 2011-3-25
Accepted: 2011-7-19
Published Online: 2011-08-30
Published in Print: 2011-10-01
©2011 by Walter de Gruyter Berlin Boston
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- Sodium butyrate induces cellular senescence in neuroblastoma and prostate cancer cells
- Investigating and critically appraising the expression and potential role of androgen receptor in breast carcinoma
- Genetic ancestry, skin reflectance and pigmentation genotypes in association with serum vitamin D metabolite balance
- Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone
- Method for regeneration of hormones: 17β-estradiol, 21α-hydroxyprogesterone and corticosterone. A pathway for a possible medical application
Schlagwörter für diesen Artikel
anti-inflammatory compound;
stereoselective synthesis;
19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone
Artikel in diesem Heft
- Original Articles
- Sodium butyrate induces cellular senescence in neuroblastoma and prostate cancer cells
- Investigating and critically appraising the expression and potential role of androgen receptor in breast carcinoma
- Genetic ancestry, skin reflectance and pigmentation genotypes in association with serum vitamin D metabolite balance
- Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone
- Method for regeneration of hormones: 17β-estradiol, 21α-hydroxyprogesterone and corticosterone. A pathway for a possible medical application
