Preparation of 24(R)- and 24(S)-5β-cholestane-3α,7α,24-triols and 25(R)- and 25(S)-5β-cholestane-3α,7α,26-triols by a hydroboration procedure

B Dayal; A K Batta; S Shefer; G S Tint; G Salen; E H Mosbach

Journal of Lipid Research (Feb 1978)

Preparation of 24(R)- and 24(S)-5β-cholestane-3α,7α,24-triols and 25(R)- and 25(S)-5β-cholestane-3α,7α,26-triols by a hydroboration procedure

B Dayal,
A K Batta,
S Shefer,
G S Tint,
G Salen,
E H Mosbach

Affiliations

B Dayal: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003
A K Batta: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003
S Shefer: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003
G S Tint: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003
G Salen: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003
E H Mosbach: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, NJ 07103; The Public Health Research Institute of the City of New York, Inc., New York, NY 10016; Veterans Administration Hospital, East Orange, NJ 07019; Cabrini Health Care Center, New York, NY 10003

Journal volume & issue: Vol. 19, no. 2
pp. 191 – 196

Abstract

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This report describes a new and convenient method for the preparation of 5β-cholestane-3α,7α,24-triol (24R and 24S) and 5β-cholestane-3α,7α,26-triol (25R and 25S) starting from 5β-cholestane-3α,7α,25-triol. Dehydration of the latter with acetic anhydride and glacial acetic acid yielded a mixture of 5β-cholest-24ene-3α,7α-diol and the corresponding Δ25 compound. Hydroboration and oxidation of the Δ24 unsaturated bile alcohol resulted in the formation of 5β-cholestane-3α,7α,24-triol. 5β-Cholestane-3α,7α,26-triol and 5β-cholestane-3α,7α-diol were obtained from the Δ25 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.

Published in Journal of Lipid Research

ISSN: 0022-2275 (Print); 1539-7262 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.journals.elsevier.com/journal-of-lipid-research

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