3β-acetoxy-5α-androstan-17β-yl dimethyl-tert-butylsilyl ether | 1415686-69-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-acetoxy-5α-androstan-17β-yl dimethyl-tert-butylsilyl ether
• CAS: 1415686-69-9
• 化学式: C₂₇H₄₈O₃Si
• 分子量: 448.762
• InChiKey: BHHGIJMSPJSWNB-WOUSRVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5α-androstan-17β-yl dimethyl-tert-butylsilyl ether 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到3β-hydroxy-5α-androstan-17β-yl dimethyltert-butylsilyl ether
  参考文献：
  名称：

  A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist

  摘要：

  We have devised an efficient procedure for the synthesis of 5 alpha-dihydrotestosterone (DHT) (1) starting from 3 beta-hydroxy-5 alpha-androstan-17-one, providing the product in unprecedented 82% yield. A reported method of using toxic Jones reagent is replaced by milder oxidizing agent (NMO/TPAP) in the synthesis of a key intermediate 17 beta-[(tert-butyldimethylsilyl)oxy]-5 alpha-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.003
• 作为产物：
  描述：

  表雄酮 在 咪唑 、 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.83h， 生成 3β-acetoxy-5α-androstan-17β-yl dimethyl-tert-butylsilyl ether
  参考文献：
  名称：

  A new simple and high-yield synthesis of 5α-dihydrotestosterone (DHT), a potent androgen receptor agonist

  摘要：

  We have devised an efficient procedure for the synthesis of 5 alpha-dihydrotestosterone (DHT) (1) starting from 3 beta-hydroxy-5 alpha-androstan-17-one, providing the product in unprecedented 82% yield. A reported method of using toxic Jones reagent is replaced by milder oxidizing agent (NMO/TPAP) in the synthesis of a key intermediate 17 beta-[(tert-butyldimethylsilyl)oxy]-5 alpha-androstan-3-one (18). This new procedure is simple, does not require special apparatus/precautions or chromatographic purification in most of the steps. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.003