4,5-epoxycholestane-3,6-diols: Templates for generating the full set of eight cholestane-3,5,6-triol stereoisomers in multigram scales, but not for a cholestane-3,4,6-triol

作者：Zhao Kejun; Wang Yongfeng^*; Han Li

来源：Steroids, 2007, 72(1): 95-104.

DOI：10.1016/j.steroids.2006.11.015

• cholestane-3,5,6-triol
• cholestane-3,4,6-triol
• 4,5-epoxycholestane-3,6-diols
• epoxide cleavage
• LiAlH4 reduction
• Lewis acid

Cholestane-3 beta,5 alpha,6 beta-triol is an extensively studied biologically important oxysterol. The full set of eight cholestane-3,5,6-triol stereoisomers was synthesised in diastereomerically pure forms by the stereoselective cleavage of eight diastereomerically pure 4,5-epoxycholestane-3,6-diols with LiAlH4, in high yields on multigram scales and without chromatography for most of them. However, applying various reportedly successful combinations of a hydride donor and a Lewis acid to the same substrates under a variety of conditions failed to generate a single unsubstituted cholestane-3,4,6-triol. The products of the eight cholestane-3,5,6-triol stereoisomers will serve as a good probe in the study of biological functions of oxysterols in a biological process.

• 出版日期2007-1
• 单位沈阳药科大学