(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol

The title steroid, C(29)H(46)O(4), is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the α face of the A–E steroidal nucleus and presents a disordered terminal CH(2)—OH group [occupancies for resolved sites are 0.591 (9)...

Descripción completa

Detalles Bibliográficos
Autores principales: Hernández Linares, María-Guadalupe, Sandoval Ramírez, Jesús, Meza Reyes, Socorro, Montiel Smith, Sara, Bernès, Sylvain
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960791/
https://www.ncbi.nlm.nih.gov/pubmed/21201948
http://dx.doi.org/10.1107/S1600536808004509
_version_ 1782188825894715392
author Hernández Linares, María-Guadalupe
Sandoval Ramírez, Jesús
Meza Reyes, Socorro
Montiel Smith, Sara
Bernès, Sylvain
author_facet Hernández Linares, María-Guadalupe
Sandoval Ramírez, Jesús
Meza Reyes, Socorro
Montiel Smith, Sara
Bernès, Sylvain
author_sort Hernández Linares, María-Guadalupe
collection PubMed
description The title steroid, C(29)H(46)O(4), is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the α face of the A–E steroidal nucleus and presents a disordered terminal CH(2)—OH group [occupancies for resolved sites are 0.591 (9) and 0.409 (9)]. The methyl group at C20 attached to ring E is also oriented toward the α face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an α,β-unsaturated ketone system, with an s-cis configuration. All hydr­oxy and carbonyl groups are involved in weak inter­molecular hydrogen bonds. The absolute configuration was assigned from the synthesis.
format Text
id pubmed-2960791
institution National Center for Biotechnology Information
language English
publishDate 2008
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29607912010-12-30 (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol Hernández Linares, María-Guadalupe Sandoval Ramírez, Jesús Meza Reyes, Socorro Montiel Smith, Sara Bernès, Sylvain Acta Crystallogr Sect E Struct Rep Online Organic Papers The title steroid, C(29)H(46)O(4), is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the α face of the A–E steroidal nucleus and presents a disordered terminal CH(2)—OH group [occupancies for resolved sites are 0.591 (9) and 0.409 (9)]. The methyl group at C20 attached to ring E is also oriented toward the α face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an α,β-unsaturated ketone system, with an s-cis configuration. All hydr­oxy and carbonyl groups are involved in weak inter­molecular hydrogen bonds. The absolute configuration was assigned from the synthesis. International Union of Crystallography 2008-02-22 /pmc/articles/PMC2960791/ /pubmed/21201948 http://dx.doi.org/10.1107/S1600536808004509 Text en © Hernández Linares et al. 2008 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
Hernández Linares, María-Guadalupe
Sandoval Ramírez, Jesús
Meza Reyes, Socorro
Montiel Smith, Sara
Bernès, Sylvain
(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title_full (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title_fullStr (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title_full_unstemmed (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title_short (E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol
title_sort (e)-(25s)-23-acetyl-5β-furost-22-ene-3β,26-diol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960791/
https://www.ncbi.nlm.nih.gov/pubmed/21201948
http://dx.doi.org/10.1107/S1600536808004509
work_keys_str_mv AT hernandezlinaresmariaguadalupe e25s23acetyl5bfurost22ene3b26diol
AT sandovalramirezjesus e25s23acetyl5bfurost22ene3b26diol
AT mezareyessocorro e25s23acetyl5bfurost22ene3b26diol
AT montielsmithsara e25s23acetyl5bfurost22ene3b26diol
AT bernessylvain e25s23acetyl5bfurost22ene3b26diol

Ejemplares similares