3β,5α,6β-Trihydroxyandrostan-17-one

3β,5α,6β-Trihydroxyandrostan-17-one

The title compound, C19H30O4, is an androstan-17-one derivative synthesized from the dehydroepiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)3 (OTf is trifluoromethanesulfonate). The six-membered rings have a sligh...

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Main Authors: L.C.R. Andrade, M.J.B.M. de Almeida, J.A. Paixão, J.F.S. Carvalho, M.L. Sá e Melo
Format: Article
Language:English
Published: International Union of Crystallography 2011-05-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536811011706
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spelling doaj-60aa743d399b46d3837ed43d0e51bbf92020-11-25T02:24:30ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682011-05-01675o1056o105710.1107/S16005368110117063β,5α,6β-Trihydroxyandrostan-17-oneL.C.R. AndradeM.J.B.M. de AlmeidaJ.A. PaixãoJ.F.S. CarvalhoM.L. Sá e MeloThe title compound, C19H30O4, is an androstan-17-one derivative synthesized from the dehydroepiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)3 (OTf is trifluoromethanesulfonate). 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 molecules 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 molecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values.http://scripts.iucr.org/cgi-bin/paper?S1600536811011706
collection DOAJ
language English
format Article
sources DOAJ
author L.C.R. Andrade
M.J.B.M. de Almeida
J.A. Paixão
J.F.S. Carvalho
M.L. Sá e Melo
spellingShingle L.C.R. Andrade
M.J.B.M. de Almeida
J.A. Paixão
J.F.S. Carvalho
M.L. Sá e Melo
3β,5α,6β-Trihydroxyandrostan-17-one
Acta Crystallographica Section E
author_facet L.C.R. Andrade
M.J.B.M. de Almeida
J.A. Paixão
J.F.S. Carvalho
M.L. Sá e Melo
author_sort L.C.R. Andrade
title 3β,5α,6β-Trihydroxyandrostan-17-one
title_short 3β,5α,6β-Trihydroxyandrostan-17-one
title_full 3β,5α,6β-Trihydroxyandrostan-17-one
title_fullStr 3β,5α,6β-Trihydroxyandrostan-17-one
title_full_unstemmed 3β,5α,6β-Trihydroxyandrostan-17-one
title_sort 3β,5α,6β-trihydroxyandrostan-17-one
publisher International Union of Crystallography
series Acta Crystallographica Section E
issn 1600-5368
publishDate 2011-05-01
description The title compound, C19H30O4, is an androstan-17-one derivative synthesized from the dehydroepiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)3 (OTf is trifluoromethanesulfonate). 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 molecules 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 molecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values.
url http://scripts.iucr.org/cgi-bin/paper?S1600536811011706
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