Steroid conjugates. Part III. Syntheses of 19-oxygenated dehydro-epi-androsterone sulphates

Abstract

Routes to the sulphate salts of several 19-hydroxy- and 19-oxo-derivatives of 3β-hydroxyandrost-5-en-17-one are described. The 19-monosulphate of the 3β,19-diol was obtained by sulphation of the 3β-monoacetate, and the 3β-monosulphate was prepared by three routes. These involved protection of the 19-hydroxy-group by formation of (a) its acetate, (b) its tetrahydropyranyl ether, and (c) the bridged 6β, 19-epoxide.