title: Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate.
abstract: THE STRUCTURE OF THE TITLE STEROID [ALTERNATIVE NAME: 3β,6β-diacet-oxy-5β-methyl-19-norcholest-9(10)-ene], C31H50O4, confirms the generally accepted mechanism for the rearrangement of a cholestan-5α-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 Δ(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 β 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).
authors.affiliation: Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, Puebla, Pue. 72570, Mexico.
authors.forename: Johana
authors.initials: J
authors.lastname: Ramírez Hernández
authors.forename: Jesús
authors.initials: J
authors.lastname: Sandoval-Ramírez
authors.forename: Socorro
authors.initials: S
authors.lastname: Meza-Reyes
authors.forename: José Luis
authors.initials: JL
authors.lastname: Vega Báez
authors.forename: Sylvain
authors.initials: S
authors.lastname: Bernès