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)
Summary
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.
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