Abstract
The X-ray crystal structure of 3β-(p-bromobenzoyloxy)-5β-cholesta-8,14-dien (space group P21, a = 10.698 A ̊, b = 9.487 A ̊, c = 15.024 A ̊, β = 96.05°, Z = 2) was determined by the heavy atom method and refined to R = 0.075. This heavy atom derivative was synthesized from 5β-cholesta-8,14-diene-3β-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 5β-H and that the configuration at C-17 was unchanged.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 273-282 |
| Number of pages | 10 |
| Journal | Chemistry and Physics of Lipids |
| Volume | 47 |
| Issue number | 4 |
| DOIs | |
| State | Published - 1988 |
| Externally published | Yes |
Keywords
- acid catalyzed isomerization
- conformational analysis
- sterol
- X-ray crystallography
ASJC Scopus subject areas
- Biochemistry
- Biophysics
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Cite this
Wilson, D. K., Wilson, W. K., Quiocho, F. A., & Schroepfer, G. J. (1988). 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. Chemistry and Physics of Lipids, 47(4), 273-282. https://doi.org/10.1016/0009-3084(88)90050-3