3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one

The title compound, C(31)H(48)O(7), a polyoxygenated steroid, was obtained by chemical oxidation of 7-de­hydro­cholesteryl acetate. The mol­ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for...

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Autores principales: Piccialli, Vincenzo, Tuzi, Angela, Oliviero, Giorgia, Borbone, Nicola, Centore, Roberto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770383/
https://www.ncbi.nlm.nih.gov/pubmed/24046668
http://dx.doi.org/10.1107/S1600536813016206
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author Piccialli, Vincenzo
Tuzi, Angela
Oliviero, Giorgia
Borbone, Nicola
Centore, Roberto
author_facet Piccialli, Vincenzo
Tuzi, Angela
Oliviero, Giorgia
Borbone, Nicola
Centore, Roberto
author_sort Piccialli, Vincenzo
collection PubMed
description The title compound, C(31)H(48)O(7), a polyoxygenated steroid, was obtained by chemical oxidation of 7-de­hydro­cholesteryl acetate. The mol­ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intra­molecular S(6) O—H⋯O hydrogen-bonding motif involving a hy­droxy donor and acceptor is observed. In the crystal, chains of mol­ecules running along the b axis are formed via O—H⋯O hydrogen bonds between hy­droxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 2(1) screw axes.
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spelling pubmed-37703832013-09-17 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one Piccialli, Vincenzo Tuzi, Angela Oliviero, Giorgia Borbone, Nicola Centore, Roberto Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(31)H(48)O(7), a polyoxygenated steroid, was obtained by chemical oxidation of 7-de­hydro­cholesteryl acetate. The mol­ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intra­molecular S(6) O—H⋯O hydrogen-bonding motif involving a hy­droxy donor and acceptor is observed. In the crystal, chains of mol­ecules running along the b axis are formed via O—H⋯O hydrogen bonds between hy­droxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 2(1) screw axes. International Union of Crystallography 2013-06-15 /pmc/articles/PMC3770383/ /pubmed/24046668 http://dx.doi.org/10.1107/S1600536813016206 Text en © Piccialli et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Piccialli, Vincenzo
Tuzi, Angela
Oliviero, Giorgia
Borbone, Nicola
Centore, Roberto
3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title_full 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title_fullStr 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title_full_unstemmed 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title_short 3β,6α-Diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
title_sort 3β,6α-diacet­oxy-5,9α-dihy­droxy-5α-cholest-7-en-11-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3770383/
https://www.ncbi.nlm.nih.gov/pubmed/24046668
http://dx.doi.org/10.1107/S1600536813016206
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