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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (23): 2637-2645. 上一篇    下一篇

研究论文

16R-溴代孕甾-3S,20S-二醇二乙酸酯与碱的条件可控性反应

林静容a 蒋世凤a 周南琰a 金荣华a 田伟生*,a,b

  

  1. (a上海师范大学资源化学实验室 上海 200234)
    (b中国科学院上海有机化学研究所 上海 200032)

  • 投稿日期:2008-02-25 修回日期:2008-06-13 发布日期:2008-12-14
  • 通讯作者: 田伟生

Controllable Reaction of 16R-Bromopregnane-3S,20S-diol Diacetate with Bases

LIN, Jing-Rong a JIANG, Shi-Feng a ZHOU, Nan-Yan a
JIN, Rong-Hua a TIAN, Wei-Sheng *,a,b
  

  1. (a Laboratory of Resource Chemistry, Shanghai Normal University, Shanghai 200234)
    (b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2008-02-25 Revised:2008-06-13 Published:2008-12-14
  • Contact: TIAN, Wei-Sheng

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为了合理利用甾体皂甙元资源, 系统地考察了16R-溴代孕甾-3S,20S-二醇二乙酸酯在不同反应条件下与碱的反应. 给出了选择性地分别转化16R-溴代孕甾-3S,20S-二醇二乙酸酯成为孕甾-16-烯-3S,20S-二醇二乙酸酯、16R-溴代孕 甾-3S,20S-二醇、孕甾-3S,16S,20S-三醇、孕甾-14,16-二烯-3S-醇乙酸酯和雄甾-16-烯-3S-醇等化合物的可控性反应结果. 这些条件可控性反应结果不仅为甾体药物和生物活性天然甾体化合物合成提供了新的合成中间体, 也为它们新合成策略和途径的设计提供了机遇.

关键词: 剑麻皂甙元, 孕甾-16-烯-3S,20S-二醇二乙酸酯, 16R-溴代孕甾-3S,20S-二醇二乙酸酯, 雄甾-16-烯-3S-醇, 条件可控性反应

The reaction of 16R-bromopregnane-3S,20S-diol diacetate with bases was investigated according to the demand of rationally utilizing steroidal sapogenins. Some useful and controllable reaction results were obtained through such investigation, in which, 16R-bromopregnane-3S,20S-diol diacetate was chemo-selec- tively converted into pregn-16-ene-3S,20S-diol diacetate, 16R-bromopregnane-3S,20S-diol, pregnane-3S,16S,20S-triol, pregne-14,16-dien-3S-ol acetate and androst-16-en-3S-ol respectively. These results not only provided new synthetic intermediates for the syntheses of steroidal drugs and natural steroids, but also presented more opportunity for the design of their new synthetic strategies and routes.

Key words: tigogenin, pregn-16-ene-3S,20S-diol diacetate, 16R-bromopregnane-3S, 20S-diol diacetate, androst-16-en-3S-ol, controllable reaction