Collect. Czech. Chem. Commun. 1996, 61, 404-412

Preparation of 7-[O-(Carboxymethyl)oxime] Derivatives of Dehydroepiandrosterone and Pregnenolone

Vladimír Pouzar, Tereza Slavíková and Ivan Černý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Novel simple syntheses of 7-(O-carboxymethyloxime) derivatives of 3β-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) and of 3β-hydroxypregn-5-en-20-one (pregnenolone) are reported. In the first one, 17-oxoandrost-5-en-3β-yl acetate was oxidized to give the 7,17-dione which was then selectively reduced in the position 17. Oximation, reoxidation, and deacetylation yielded the desired oxime. The second synthesis started with (20R)-pregn-5-ene-3β,20-diol 3-acetate which was converted to the 20-nitrate, oxidized to the C-7 ketone, oximated, partially deprotected in position 20, reoxidized, and deacetylated. Both the 7-(O-carboxymethyloxime) derivatives have been devised as immunoassay components.

Keywords: Steroid haptens; NMR spectra; Synthesis.