Acta Chimica Sinica ›› 2011, Vol. 69 ›› Issue (19): 2272-2280. Previous Articles     Next Articles

Full Papers



  1. (1上海师范大学资源化学实验室 上海 200234)
    (2中国科学院上海有机化学研究所 上海 200032)
  • 投稿日期:2011-03-13 修回日期:2011-05-04 发布日期:2011-05-27
  • 通讯作者: 林静容
  • 基金资助:


Synthesis of 16S,20S-Epoxypregnane-3S-ol Acetate and Its Regioselective Epoxide-opening Substitution

Han Jun1 Lin Jingrong*,1 Jin Ronghua1 Tian Weisheng*,1,2   

  1. (1 Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234)
    (2 Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2011-03-13 Revised:2011-05-04 Published:2011-05-27
  • Contact: LIN JingRong
  • Supported by:

    The project supported by Innovation Program of Shanghai Municipal Education Commission

A synthetic method of 16S,20S-epoxypregnane-3S-ol acetate (4b) from pregnane-3S,16S, 20S-triol was developed. Then the epoxide-opening reaction of 4b was investigated under different conditions. The research results showed that 16S,20S-epoxypregnane-3S-ol acetate was chemo-selectively converted into 20R-bromopregnane-3S,16S-diol diacetate, 20R-bromopregnane-3S,16S-diol-3-acetate, 20R-chloropregnane-3S,16S-diol diacetate, 20R-iodopregnane-3S,16S-diol-3-acetate and pregnane-3S, 16S,20R-triol-3-acetate. These results not only provided new synthetic intermediates for the syntheses of steroidal drugs and natural steroids, but also presented epoxide-opening methods of steroids with an asymmetric oxetane ring.

Key words: tigogenin, pregnane-3S,16S,20S-triol, 16S,20S-epoxypregnane-3S-ol acetate, epoxide-opening, synthesis