Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids
Publication type: Journal Article
Publication date: 1981-10-01
scimago Q2
wos Q3
SJR: 0.620
CiteScore: 4.3
Impact factor: 2.3
ISSN: 0039128X, 18785867
PubMed ID:
7314161
Organic Chemistry
Biochemistry
Molecular Biology
Pharmacology
Clinical Biochemistry
Endocrinology
Abstract
Interest in the structural requirements of a sterol or bile acid for maximal activity by an hepatic microsomal steroid 12 alpha-hydroxylase prompted the preparation of 5 alpha-cholestane-3 alpha, 7 alpha, 25-triol and 5 alpha-analogs of 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-carboxylic acid. Methyl 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-carboxylate derived from methyl chenodeoxycholate via the Arndt-Eistert reaction was allomerized with Raney nickel in boiling p-cymene to provide a number of product of which methyl 3, 7-dioxo-5 beta- and 5 alpha-cholane-24-carboxylates, methyl 3-oxo-7 alpha-hydroxy-5 beta-and 5 alpha-cholane-24-carboxylates, were identified. Reduction with K-Selectride of methyl 3-oxo-7 alpha-hydroxy-5 beta-cholane-24-carboxylate, provided a high yield of methyl 3 alpha, 7 alpha-dihydroxy-5 alpha-cholane-24-carboxylate. Treatment of this ester with an excess of methyl magnesium iodide afforded 5 alpha-cholestane-3 alpha, 7 alpha, 25-triol. The products were characterized by thin-layer and gas liquid chromatography, proton resonance, infrared and mass spectrometry.
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Hiremath S. V., Elliott W. H. Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids // Steroids. 1981. Vol. 38. No. 4. pp. 465-475.
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Hiremath S. V., Elliott W. H. Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids // Steroids. 1981. Vol. 38. No. 4. pp. 465-475.
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RIS
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TY - JOUR
DO - 10.1016/0039-128x(81)90080-5
UR - https://doi.org/10.1016/0039-128x(81)90080-5
TI - Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids
T2 - Steroids
AU - Hiremath, S V
AU - Elliott, William H.
PY - 1981
DA - 1981/10/01
PB - Elsevier
SP - 465-475
IS - 4
VL - 38
PMID - 7314161
SN - 0039-128X
SN - 1878-5867
ER -
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BibTex (up to 50 authors)
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@article{1981_Hiremath,
author = {S V Hiremath and William H. Elliott},
title = {Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids},
journal = {Steroids},
year = {1981},
volume = {38},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016/0039-128x(81)90080-5},
number = {4},
pages = {465--475},
doi = {10.1016/0039-128x(81)90080-5}
}
Cite this
MLA
Copy
Hiremath, S. V., and William H. Elliott. “Bile acids. LXIV. Synthesis of 5α-cholestane-3α,7α,25-triol and esters of new 5α-bile acids.” Steroids, vol. 38, no. 4, Oct. 1981, pp. 465-475. https://doi.org/10.1016/0039-128x(81)90080-5.