(25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate

The title steroid, C(34)H(50)O(6)S, is an inter­mediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2α,3α-diol functionality. The polycyclic spiro­stan system has the expected conformation, with six-membered rings adopting chair forms and...

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Autores principales: Fernández-Herrera, María A., Sandoval-Ramírez, Jesús, Bernès, Sylvain, Rodríguez-Acosta, Maricela, Hernández Linares, María-Guadalupe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3589000/
https://www.ncbi.nlm.nih.gov/pubmed/23476236
http://dx.doi.org/10.1107/S1600536812046600
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author Fernández-Herrera, María A.
Sandoval-Ramírez, Jesús
Bernès, Sylvain
Rodríguez-Acosta, Maricela
Hernández Linares, María-Guadalupe
author_facet Fernández-Herrera, María A.
Sandoval-Ramírez, Jesús
Bernès, Sylvain
Rodríguez-Acosta, Maricela
Hernández Linares, María-Guadalupe
author_sort Fernández-Herrera, María A.
collection PubMed
description The title steroid, C(34)H(50)O(6)S, is an inter­mediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2α,3α-diol functionality. The polycyclic spiro­stan system has the expected conformation, with six-membered rings adopting chair forms and the five-membered rings envelope forms (flap atoms are the methine C atom in the C/D-ring junction and the spiro C atom connecting rings E and F). The 3β-tosyl­ate group is oriented in such a way that S=O bonds are engaged in inter­molecular hydrogen bonds with O—H and C—H donors. Chains of mol­ecules are formed along [100] via O—H⋯O hydrogen bonds, and secondary weak C—H⋯O inter­actions connect two neighbouring chains in the [001] direction.
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spelling pubmed-35890002013-03-08 (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate Fernández-Herrera, María A. Sandoval-Ramírez, Jesús Bernès, Sylvain Rodríguez-Acosta, Maricela Hernández Linares, María-Guadalupe Acta Crystallogr Sect E Struct Rep Online Organic Papers The title steroid, C(34)H(50)O(6)S, is an inter­mediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2α,3α-diol functionality. The polycyclic spiro­stan system has the expected conformation, with six-membered rings adopting chair forms and the five-membered rings envelope forms (flap atoms are the methine C atom in the C/D-ring junction and the spiro C atom connecting rings E and F). The 3β-tosyl­ate group is oriented in such a way that S=O bonds are engaged in inter­molecular hydrogen bonds with O—H and C—H donors. Chains of mol­ecules are formed along [100] via O—H⋯O hydrogen bonds, and secondary weak C—H⋯O inter­actions connect two neighbouring chains in the [001] direction. International Union of Crystallography 2012-11-24 /pmc/articles/PMC3589000/ /pubmed/23476236 http://dx.doi.org/10.1107/S1600536812046600 Text en © Fernández-Herrera et al. 2012 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
Fernández-Herrera, María A.
Sandoval-Ramírez, Jesús
Bernès, Sylvain
Rodríguez-Acosta, Maricela
Hernández Linares, María-Guadalupe
(25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title_full (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title_fullStr (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title_full_unstemmed (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title_short (25R)-6α-Hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
title_sort (25r)-6α-hy­droxy-5α-spiro­stan-3β-yl tosyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3589000/
https://www.ncbi.nlm.nih.gov/pubmed/23476236
http://dx.doi.org/10.1107/S1600536812046600
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