Crystal structure of 3β-benzoyloxy-6α-chloro-5α-cholest-7-ene, a key intermediate 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

2 Citations (Scopus)

Abstract

The X-ray crystal structure of 3β-benzoyloxy-6α-chloro-5α-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, β = 99.43°, 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.

Original languageEnglish (US)
Pages (from-to)283-289
Number of pages7
JournalChemistry and Physics of Lipids
Volume47
Issue number4
DOIs
StatePublished - 1988
Externally publishedYes

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Benzoates
Chlorine
Isomerization
Crystal structure
X-Rays
X rays
Atoms
Acids
cholest-8(14)-en-3-ol-15-one

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics

Cite this

Crystal structure of 3β-benzoyloxy-6α-chloro-5α-cholest-7-ene, a key intermediate 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. 283-289.

Research output: Contribution to journalArticle

Wilson, David K. ; Wilson, William K. ; Quiocho, Florante A. ; Schroepfer, George J. / Crystal structure of 3β-benzoyloxy-6α-chloro-5α-cholest-7-ene, a key intermediate 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. 283-289.
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abstract = "The X-ray crystal structure of 3β-benzoyloxy-6α-chloro-5α-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, β = 99.43°, 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.",
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AU - Wilson, William K.

AU - Quiocho, Florante A.

AU - Schroepfer, George J.

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AB - The X-ray crystal structure of 3β-benzoyloxy-6α-chloro-5α-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, β = 99.43°, 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.

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