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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-3770383 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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