3β,5α,6β-Trihy-droxy-androstan-17-one

Abstract

The title compound, C(19)H(30)O(4), is an androstan-17-one derivative synthesized from the dehydro-epiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)(3) (OTf is trifluoro-methane-sulfonate). The six-membered rings have a slightly flattened chair conformation, while the five-membered ring adopts a 14-α envelope conformation. All rings are trans fused. In the crystal, the mol-ecules are connected by O-H⋯O hydrogen bonds involving the hydroxyl and carbonyl groups, forming a three-dimensional network. A quantum mechanical ab initio Roothan Hartree-Fock calculation of the free mol-ecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values.