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

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.