(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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Detalles Bibliográficos
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
Descripción
Sumario: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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