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Acta Cryst. (2012). E68, o3331
[ doi:10.1107/S1600536812045278 ]

Westphalen's diol diacetate: 19(10[rightwards arrow]5)-abeo-5[beta]-cholest-9-ene-3[beta],6[beta]-diyl diacetate

J. Ramírez Hernández, J. Sandoval-Ramírez, S. Meza-Reyes, J. L. Vega Báez and S. Bernès

Abstract: The structure of the title steroid [alternative name: 3[beta],6[beta]-diacetoxy-5[beta]-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5[alpha]-ol derivative reported a century ago by Westphalen. The methyl group at position 10 of the starting material migrates to position 5 in the steroidal nucleus, while a [Delta]9 bond is formed, as indicated by the C=C bond length of 1.347 (4) Å. The methyl transposition leaves the 5R configuration unchanged, with the methyl oriented towards the [beta] face. During the rearrangement, the steroidal B ring experiences a conformational distortion from chair to envelope with the C atom at position 6 as the flap. In the title structure, the isopropyl group of the side chain is disordered over two positions, with occupancies of 0.733 (10) and 0.267 (10). The carbonyl O atom in the acetyl group at C3 is also disordered with an occupancy ratio of 0.62 (4):0.38 (4).


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