Crystal structure of 3 beta-benzoyloxy-6 alpha-chloro-5 alpha-cholest-7-ene, a key intermediate in the chemical synthesis of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one.
The X-ray crystal structure of 3 beta-benzoyloxy-6 alpha-chloro-5 alpha-cholest-7-ene (IV) was determined by the heavy atom method and refined to R = 0.063 (space group P21, a = 11.364, b = 11.089, c = 12.232, beta = 99.43 degrees, Z = 2). IV was previously shown to be an important intermediate in the acid-catalyzed isomerization of 7-dehydrocholesteryl benzoate. The present work unequivocally establishes the location of the double bond and the configuration of the chlorine of IV, information which is essential to the correct formulation of the mechanism of this reaction.
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*; D002782:Cholestenes / Q000138:chemical synthesis*; D002783:Cholestenones / Q000138:chemical synthesis*; D003461:Crystallography; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013696:Temperature
D000924:Anticholesteremic Agents; D002782:Cholestenes; D002783:Cholestenones; C057790:3-benzoyloxy-6-chlorocholest-7-ene; C015073:cholest-8(14)-en-3-ol-15-one