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

doi:10.1016/0009-3084(88)90050-3

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 journal › Article

8 Scopus citations

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	https://doi.org/10.1016/0009-3084(88)90050-3
State	Published - 1988
Externally published	Yes

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Keywords

acid catalyzed isomerization
conformational analysis
sterol
X-ray crystallography

ASJC Scopus subject areas

Biochemistry
Biophysics

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

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title = "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",

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.",

keywords = "acid catalyzed isomerization, conformational analysis, sterol, X-ray crystallography",

author = "Wilson, {David K.} and Wilson, {William K.} and Quiocho, {Florante A.} and Schroepfer, {George J.}",

year = "1988",

doi = "10.1016/0009-3084(88)90050-3",

language = "English (US)",

volume = "47",

pages = "273--282",

journal = "Chemistry and Physics of Lipids",

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T1 - 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

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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U2 - 10.1016/0009-3084(88)90050-3

DO - 10.1016/0009-3084(88)90050-3

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VL - 47

SP - 273

EP - 282

JO - Chemistry and Physics of Lipids

JF - Chemistry and Physics of Lipids

SN - 0009-3084

IS - 4

ER -

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10.1016/0009-3084(88)90050-3