SYNTHESIS OF 5BETA-CHOLESTANE-3ALPHA, 7ALPHA, 12ALPHA, 25-TETROL AND 5BETA-CHOLESTANE-3ALPHA, 7ALPHA, 12ALPHA, 24XI, 25-PENTOL

  • 1 January 1976
    • journal article
    • research article
    • Vol. 17  (1) , 74-77
Abstract
This paper describes syntheses of 5.beta.-cholestane-3.alpha.,7.alpha.,12.alpha.,25-tetrol and 5.beta.-cholestane-3.alpha.,7.alpha.,12.alpha.,24.xi.,25-pentol which give higher yields than previously published methods. 5.beta.-Cholestane-3.alpha.,7.alpha.,12.alpha.,24.xi.,25-pentol was synthesized by a different procedure, i.e., via performic acid oxidation of the corresponding unsaturated triol, which gave a lower yield but avoided the formation of 5.beta.-cholestane-3.alpha.,7.alpha.,12.alpha.,25,26-pentol, which normally tends to contaminate the final product. Structures were confirmed by GLC, IR-, PMR and mass spectrometry. 5.beta.-Cholestane-3.alpha.,7.alpha.,12.alpha.,25-tetrol and 5.beta.-cholestane-3.alpha.,7.alpha.,12.alpha.,24.xi.,25-pentol were required for in vivo and in vitro studies of the (hypothetical) 25-hydroxylation pathway of cholic acid biosynthesis.

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