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

David K. Wilson, William K. Wilson, Florante A. Quiocho, George J. Schroepfer

Research output: Contribution to journalArticle

8 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)273-282
Number of pages10
JournalChemistry and Physics of Lipids
Volume47
Issue number4
DOIs
StatePublished - 1988
Externally publishedYes

Fingerprint

Benzoates
Isomerization
Byproducts
Atoms
Chloroform
Esters
Crystal structure
X-Rays
Derivatives
X rays
Temperature
cholest-8(14)-en-3-ol-15-one

Keywords

  • acid catalyzed isomerization
  • conformational analysis
  • sterol
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

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. / Wilson, David K.; Wilson, William K.; Quiocho, Florante A.; Schroepfer, George J.

In: Chemistry and Physics of Lipids, Vol. 47, No. 4, 1988, p. 273-282.

Research output: Contribution to journalArticle

Wilson, David K. ; Wilson, William K. ; Quiocho, Florante A. ; Schroepfer, George J. / 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. In: Chemistry and Physics of Lipids. 1988 ; Vol. 47, No. 4. pp. 273-282.
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AU - Wilson, David K.

AU - Wilson, William K.

AU - Quiocho, Florante A.

AU - Schroepfer, George J.

PY - 1988

Y1 - 1988

N2 - 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.

AB - 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.

KW - acid catalyzed isomerization

KW - conformational analysis

KW - sterol

KW - X-ray crystallography

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