Concerning the structure of 3 beta-benzoyloxy-5 beta-cholesta-8,14-diene, a major byproduct in the chemical synthesis of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one.
The X-ray crystal structure of 3 beta-(p-bromobenzoyloxy)-5 beta-cholesta-8,14-diene (space group P21, a = 10.698 A, b = 9.487 A, c = 15.024 A, beta = 96.05 degrees, Z = 2) was determined by the heavy atom method and refined to R = 0.075. This heavy atom derivative was synthesized from 5 beta-cholesta-8,14-diene-3 beta-ol, the benzoate ester of which was previously shown to be the major byproduct in the low-temperature isomerization of 7-dehydrocholesteryl benzoate in HCl/chloroform. The work presented here establishes unequivocally that the configuration of this isomerization byproduct at C-5 is 5 beta-H and that the configuration at C-17 was unchanged.
Wilson
D K
DK
Department of Biochemistry, Rice University, Houston, TX 77251.
Wilson
W K
WK
Quiocho
F A
FA
Schroepfer
G J
GJ
D000924:Anticholesteremic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002775:Cholestadienols / Q000138:chemical synthesis*; D002782:Cholestenes / Q000138:chemical synthesis*; D002783:Cholestenones / Q000138:chemical synthesis*; D003461:Crystallography; D008968:Molecular Conformation
D000924:Anticholesteremic Agents; D002775:Cholestadienols; D002782:Cholestenes; D002783:Cholestenones; C057788:3-benzoyloxycholesta-8,14-diene; C015073:cholest-8(14)-en-3-ol-15-one