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化学学报
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化学学报 ›› 1976, Vol. 34 ›› Issue (4): 301-307. 上一篇    下一篇

论文

双炔失碳酯(抗孕-53)的化学合成

  

  1. 1. 上海第十九制药厂;
    2. 四川医学院;
    3. 上海医药工业研究院
  • 投稿日期:1976-09-30 发布日期:2013-06-03

SYNTHESIS OF 2α, 17α-DIETHYNYL-A-NOR-5α-ANDROSTANE-2β, 17β-DIOL DIPROPIONATE(ANORDRIN)

  1. 1. SHANGHAI NO.19 PHARMACEUTICAL WORKS;
    2. SZECHUAN MEDICAL COLLEGE;
    3. SHANGHAI INSTITUTE OF MEDICINAL INDUSTRIES
  • Received:1976-09-30 Published:2013-06-03

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A环失碳的甾族化合物双炔失碳酯(ANORDRIN,2α-17α-diethynyl-A-nor-5α-androstane,2β,17β-dioldipropionate)是一种新的口服避孕药,对多种动物及人具有显著的抗生育作用.我们利用去氢表雄酮醋酸酯为原料,经六步反应获得了成品;并对氧化裂环、乙炔化和丙酰化各步反应条件作了研究.改进后的合成总收率为35%.利用核磁共振测定确定了双炔失碳酯C2位炔基的构型.

ANORDRIN (2α, 17α-diethynyl, A-nor-5α-androstane, 2β,17β-diol dipropionate) is a new oral contraceptive which possesses a significant anti-fertility action in various kinds of animals and human being. Starting from dehydro-epiandrosterone acetate the desired product has been synthesized in 6 steps with an over-all yield of 35%. By means of NMR, study the configuration of the C2 ethynyl group in Anordrin is assigned as α.