Synthesis of a 19-(O-carboxymethyl)oxime hapten of 7β-hydroxy-epiandrosterone

Clotilde Ferroud 1 , Gilbert Revial 1 , Christophe Ricco 1 , Olivier Hennebert 2  and Robert Morfin 2
  • 1 Laboratoire de Transformation Chimique et Pharmaceutique, ERL3193 CNRS/ESPCIParisTech/Cnam, 2 rue Conté, 75003 Paris, France
  • 2 Laboratoire de Biologie EA3199 Conservatoire national des arts et métiers, 2 rue Conté, 75003 Paris, France

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.

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Hormone Molecular Biology and Clinical Investigation is dedicated to the provision of data on molecular aspects of hormones in physiology and pathophysiology. The journal covers the treatment of diseases, such as endocrine cancers, renal and lymphoid carcinoma, hypertension, cardiovascular systems, osteoporosis, hormone deficiency in menopause and andropause, obesity, diabetes, brain and related diseases.

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