(8R,9S,10R,13S,14S,17S)-3-Amino-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol | 95529-45-6

• 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: (8R,9S,10R,13S,14S,17S)-3-Amino-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
• CAS: 95529-45-6
• 化学式: C₁₉H₃₁NO
• 分子量: 289.461
• InChiKey: FCUGCTSXLBPRJB-SSCHMFMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S,17S)-3-Amino-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol 在 吡啶 、 盐酸 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 正丁醇 为溶剂， 反应 33.0h， 生成 3α-(6'-diethylaminopurin-9'-yl)-androst-4-en-17β-ol
  参考文献：
  名称：

  Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17β-ol

  摘要：

  Steroidal nucleoside analogs were synthesized starting from testosterone. By reduction of the oxime of 17beta-hydroxy-androst-4-en-3-one (testosterone), a mixture of the two amino epimers of C-3 were obtained. The 3alpha-amino-androst-4-en-17beta-ol was crystallized in 73% yield and coupled with 5-amino-4,6-dichloropyrimidine to give 3alpha-(5'-amino-4'-chloro-pyrimidin-6'-yl)amino-androst-4-en-17beta-ol. This compound was treated with triethyl orthoformate in acid media to give the corresponding purinyl steroid adduct 3alpha-(6'-chloro-purin-9'-yl)-androst-4-en- 17beta-ol in 98% yield. This substance, in turn, was converted with good yield into the 6'-thio, 6'-methylamino, and 6'-diethyl aminopurinyl derivatives through nucleophilic reactions at C-6 of the purine nucleus. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00157-x
• 作为产物：
  描述：

  睾酮 在 吡啶 、 盐酸羟胺 、 sodium 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 3.0h， 生成 (8R,9S,10R,13S,14S,17S)-3-Amino-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol
  参考文献：
  名称：

  Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17β-ol

  摘要：

  Steroidal nucleoside analogs were synthesized starting from testosterone. By reduction of the oxime of 17beta-hydroxy-androst-4-en-3-one (testosterone), a mixture of the two amino epimers of C-3 were obtained. The 3alpha-amino-androst-4-en-17beta-ol was crystallized in 73% yield and coupled with 5-amino-4,6-dichloropyrimidine to give 3alpha-(5'-amino-4'-chloro-pyrimidin-6'-yl)amino-androst-4-en-17beta-ol. This compound was treated with triethyl orthoformate in acid media to give the corresponding purinyl steroid adduct 3alpha-(6'-chloro-purin-9'-yl)-androst-4-en- 17beta-ol in 98% yield. This substance, in turn, was converted with good yield into the 6'-thio, 6'-methylamino, and 6'-diethyl aminopurinyl derivatives through nucleophilic reactions at C-6 of the purine nucleus. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00157-x