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Journal of Lipid Research, Vol 17, 478-484, Copyright © 1976 by Lipid Research, Inc.

ARTICLES

C26-Analogs of naturally occurring C27 bile alcohols

B Dayal, S Shefer, GS Tint, G Salen and EH Mosbach

C26 Bile of the 24-nor-5beta-cholestane series were prepared starting from methyl cholate. A Grignard reaction of methyl magnesium iodide with methyl cholate yielded 24-nor-5beta-cholestane-3alpha, 7alpha, 12alpha, 25-tetrol which was dehydrated TO FORM a mixture of 24-nor- 5beta-cholest-23-ene-3alpha, 7alpha, 12 alpha-triol and the corresponding delta25 compound. Oxidation of the former with OsO4 yielded 24-nor-5beta-cholestane-3alpha, 7alpha, 12alpha, 23epsilon, 25pentol, while catalytic hydrogenation of a mixture of the delta23 and delta25 triols resulted in the formation of 24-nor-5beta-cholestane-3- alpha-, 7alpha-12alpha-triol. The structures of these new compounds were confirmed by infrared and nuclear megnetic resonance spectrometry and by gas-liquid chromatography-mass spectrometry.
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