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化学学报
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化学学报 ›› 1966, Vol. 32 ›› Issue (1): 58-63. 上一篇    下一篇

论文

甾体化合物——XLⅧ.以高锰酸钾使△5, 16, 20-孕甾三烯-3β, 20-二醇二乙酸酯羟基化

王资武, 黄鸣龙   

  1. 中国科学院有机化学研究所
  • 投稿日期:1965-03-05 发布日期:2013-06-03

STEROIDS——XLⅧ. THE HYDROXYLATION OF Δ5, 16, 20-PREGNATRIEN-3β, 20-DIOL DIACETATE BY POTASSIUM PERMANGANATE

WANG Zi-Wu, HUANG Minlon   

  1. Institute of Organic Chemistry, Academia Sinica
  • Received:1965-03-05 Published:2013-06-03

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△5,16,20-孕甾三烯-3β,20-二醇二乙酸酯(Ⅴ)经高锰酸钾处理而获得一羟基化产物,此物的结构经初步推定为X,而不是前人所拟的VI.四醇化合物(Ⅷ)用丙酮-高氯酸处理所得的缩丙酮化合物经证明为ⅩⅡ,而文献报导此反应生成ⅩⅢ可能是不正确的.ⅩⅢ已经另从Ⅸ合成.这些结果使我们怀疑其他一些具16α,17α,21-三羟-20-酮结构的甾体化合物与丙酮反应生成16,17-缩丙酮化合物的推定的正确性.

1.On treating -pregnatrien-3β,20-diol diacetate (Ⅴ) with potassium permanganate a hydroxylation product was obtained.Its structure has been assumed to be Ⅹ instead of Ⅵ as proposed previously.2.When the tetrol (Ⅷ) was treated with acetone-perchloric acid,it formed the acetonide ⅩⅡ,but not ⅩⅢ as reported in the literature.The latter was prepared from another route starting with Ⅵ.Based on these results we suspect the correctness of the assumption that 16α,17α,21-trihydroxy-20-keto steroids form 16,17-acetonides under the described conditions.