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 |
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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 journal › Article
}
TY - JOUR
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
UR - http://www.scopus.com/inward/record.url?scp=0024066730&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0024066730&partnerID=8YFLogxK
U2 - 10.1016/0009-3084(88)90050-3
DO - 10.1016/0009-3084(88)90050-3
M3 - Article
C2 - 3191559
AN - SCOPUS:0024066730
VL - 47
SP - 273
EP - 282
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
SN - 0009-3084
IS - 4
ER -