Collect. Czech. Chem. Commun. 1996, 61, 288-297

Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols

Vladimír Pouzar and Ivan Černý

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


New approach to the preparation of steroids with connecting bridge, based on an O-carboxymethyloxime (CMO) structure, and with terminal hydroxy group, is presented. 17-CMO derivatives of 3β-acetoxy- and 3β-methoxymethoxyandrost-5-en-17-one were condensed with α,ω-amino alcohols to give derivatives with a chain of seven to nine atoms. After THP-protection, these compounds were converted to 3-keto-4-ene derivatives. An alternative synthesis consisted in transformation of 17-CMO derivatives with bonded amino acids by reduction of the terminal carboxyl. The resulting compounds were designed as building blocks for the preparation of bis-haptens for sandwich immunoassays.

Keywords: Steroid synthesis; Haptens; Connecting bridge.