22 research outputs found
3ÎČ,5α,6ÎČ-TrihyÂdroxyÂandrostan-17-one
The title compound, C19H30O4, is an androstan-17-one derivative synthesized from the dehydroÂepiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)3 (OTf is trifluoroÂmethaneÂsulfonate). 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 molÂecules are connected by OâHâŻO hydrogen bonds involving the hydroxyl and carbonyl groups, forming a three-dimensional network. A quantum mechanical ab initio Roothan HartreeâFock calculation of the free molÂecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values