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Concerning the structure of 3β-benzoyloxy-5β-cholesta-8,14-diene, a major byproduct in the chemical synthesis of 5α-cholest-8(14)-en-3β-ol-15-one

✍ Scribed by David K. Wilson; William K. Wilson; Florante A. Quiocho; George J. Schroepfer Jr.

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
659 KB
Volume
47
Category
Article
ISSN
0009-3084

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✦ Synopsis

The X-ray crystal structure of 3~-(p-bromobenzoyloxy)-5~-cholesta-8,14-diene (space group P21, a = 10.698 ,/~, b = 9.487 .~, c = 15.024 A, ~ = 96.05 °, Z = 2) was determined by the heavy atom method and refined to R = 0.075. This heavy atom derivative was synthesized from 5~-cholesta-8,14-dien-31~-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/chioroform. The work presented here establishes unequivocally that the conf'q~uration of this isomerization byproduct at C-5 is 5~-H and that the configuration at C-17 was unchanged.

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