Abstract

The title steroid, C34H50O6S, 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.

Highlights

  • The title steroid, C34H50O6S, is an intermediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2,3-diol functionality

  • The 3-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

  • For the hydroboration-oxidation synthetic step used for the preparation of the title compound, see: Smith & Pelter (1991); Brown (1962)

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Summary

Structure Reports

Marıa-Guadalupe Hernández Linaresd a Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Quımicas, Ciudad Universitaria, Puebla, Pue. 72570, Mexico, bUniversidad Autónoma de. Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico, cHerbario y.

Data collection
Related literature
Mo K radiation
Findings
Graphite monochromator ω scans
Full Text
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