Synthesis of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol

Autor: Dayal, B, Shefer, S, Tint, G S, Salen, G, Mosbach, E H
Zdroj: Journal of Lipid Research; January 1976, Vol. 17 Issue: 1 p74-77, 4p
Abstrakt: This paper describes syntheses of 5β-cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol which give higher yields than previously published methods. In addition, 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol was synthesized by a different procedure, namely via performic acid oxidation of the correspinding unsaturated triol, which gave a lower yield but avoided the formation of 5β-cholestane-3α, 7α, 12α, 25, 26-pentol, which normally tends to contaminate the final product. Structures were confirmed by gas-liquid chromatography, infrared-, proton magnetic resonance- and mass spectrometry, 5β-Cholestane-3α, 7α, 12α, 25-tetrol and 5β-cholestane-3α, 7α, 12α, 24ξ, 25-pentol were required for in vivo and in vitro studies of the (hypothetical) 25-hydroxylation pathway of cholic acid biosynthesis.
Databáze: Supplemental Index