C26-Analogs of naturally occurring C27 bile alcohols

B Dayal; S Shefer; G S Tint; G Salen; E H Mosbach, Ph.D.

Journal of Lipid Research (Sep 1976)

C26-Analogs of naturally occurring C27 bile alcohols

B Dayal,
S Shefer,
G S Tint,
G Salen,
E H Mosbach, Ph.D.

Affiliations

B Dayal: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Veterans Administration Hospital, East Orange, N.J. 07019; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016
S Shefer: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Veterans Administration Hospital, East Orange, N.J. 07019; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016
G S Tint: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Veterans Administration Hospital, East Orange, N.J. 07019; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016
G Salen: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Veterans Administration Hospital, East Orange, N.J. 07019; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016
E H Mosbach, Ph.D.: Department of Medicine, College of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, N.J. 07103; The Veterans Administration Hospital, East Orange, N.J. 07019; The Public Health Research Institute of the City of New York, Inc., New York, N.Y. 10016; Public Health Research Institute, 455 First Avenue, New York, N.Y. 10016; Address reprint requests to Erwin H. Mosbach, Ph.D.

Journal volume & issue: Vol. 17, no. 5
pp. 478 – 484

Abstract

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C26 Bile of the 24-nor-5β-cholestane series were prepared starting from methyl cholate. A Grignard reaction of methyl magnesium iodide with methyl cholate yielded 24-nor-5β-cholestane-3α,7α,12α,25-tetrol which was dehydrated to form a mixture of 24-nor-5β-cholest-23-ene-3α,7α,12α-triol and the corresponding Δ25 compound. Oxidation of the former with OsO4 yielded 24-nor-5β-cholestane-3α,7α,12α,23ξ,25-pentol, while catalytic hydrogenation of a mixture of the Δ23 and Δ25 triols resulted in the formation of 24-nor-5β-cholestane-3-α,7α,-12α-triol. The structures of these new compounds were confirmed by infrared and nuclear megnetic resonance spectrometry and by gas–liquid chromatography–mass spectrometry.

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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