Collect. Czech. Chem. Commun. 1997, 62, 457-470

Syntheses of Steroid O-(3-Carboxypropyl)oximes

Tereza Slavíková, Vladimír Pouzar and Ivan Černý

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


The syntheses of O-(3-carboxypropyl)oxime derivatives, i.e. bis-homologues of O-(carboxymethyl)oxime derivatives (CMO), derived from dehydroepiandrosterone, testosterone and estradiol are presented. Both the reaction of steroid ketone with O-(3-carboxypropyl)hydroxylamine, and the reaction of sodium salt of steroid oxime with ethyl 4-bromobutyrate were alternatively evaluated, together with some other methods using successive chain lengthening. The compatibility with acetyl and methoxymethyl protecting groups was studied.

Keywords: O-Alkylated oximes; E/Z Isomers.