Document Detail


Preparation of 24(R)- and 24(S)-5beta-cholestane-3alpha,7alpha,24-triols and 25(R)- and 25(S)-5beta-cholestane-3alpha,7alpha,26-triols by a hydroboration procedure.
MedLine Citation:
PMID:  632683     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
This report describes a new and convenient method for the preparation of 5beta-cholestane-3alpha,7alpha,24-triol (24R and 24S) and 5beta-cholestane-3alpha,7alpha,26-triol (25R and 25S) starting from 5beta-cholestane-3alpha,7alpha,25-triol. Dehydration of the latter with acetic anhydride and glacial acetic acid yielded a mixture of 5beta-cholest-24ene-3alpha,7alpha-diol and the corresponding delta25 compound. Hydroboration and oxidation of the delta24 unsaturated bile alcohol resulted in the formation of 5beta-cholestane-3alpha,7alpha,24-triol. 5beta-Cholestane-3alpha,7alpha,26-triol and 5beta-cholestane-3alpha,7alpha-diol were obtained from the delta25 bile alcohol. In each case the bile alcohols epimeric at C-24 and C-25 were resolved by analytical and preparative thin-layer chromatography and characterized by gas-liquid chromatography, infrared-, proton magnetic resonance-, and mass spectrometry. Tentative assignment of the 24R, 24S and 25R, 25S configurations was made on the basis of molecular rotation differences. These epimeric bile alcohols will be useful for biological studies of chenodeoxycholic acid biosynthesis.
Authors:
B Dayal; A K Batta; S Shefer; G S Tint; G Salen; E H Mosbach
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of lipid research     Volume:  19     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1978 Feb 
Date Detail:
Created Date:  1978-05-08     Completed Date:  1978-05-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  191-6     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Borohydrides
Cholestanols / chemical synthesis*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methods
Molecular Conformation
Chemical
Reg. No./Substance:
0/Borohydrides; 0/Cholestanols

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