(20S)-3β-<(tert-butyldimethylsilyl)oxy>-5α-cholestan-15,23-dione

• 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: (20S)-3β-<(tert-butyldimethylsilyl)oxy>-5α-cholestan-15,23-dione
• 英文别名: (3S,5S,8R,9S,10S,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-17-[(2S)-6-methyl-4-oxoheptan-2-yl]-1,2,3,4,5,6,7,8,9,11,12,14,16,17-tetradecahydrocyclopenta[a]phenanthren-15-one
• 化学式: C₃₃H₅₈O₃Si
• 分子量: 530.907
• InChiKey: WMUPWJXIGFDJDG-AWSSYRFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.86
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3β-<(tert-butyldimethylsilyl)oxy>-15β-hydroxy-24-nor-5α-cholane-23-nitrile 在 sodium hydroxide 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 (20S)-3β-<(tert-butyldimethylsilyl)oxy>-5α-cholestan-15,23-dione
  参考文献：
  名称：

  Synthesis of the C/D/E and A/B Rings of Xestobergsterol-(A)

  摘要：

  The A/B and the C/D/E rings of the xestobergsterol skeleton have been stereoselectively synthesized starting with testosterone and epiandrosterone, respectively. A deconjugative ketalization of the A-ring enone of testosterone provided a handle for functionalization of the B-ring. A stereoselective aldol condensation was used to incorporate the E-ring.

  DOI：

  10.1021/jo982319w

文献信息

• Synthesis of the C/D/E and A/B Rings of Xestobergsterol-(A)
  作者：M. E. Krafft、O. A. Dasse、Z. Fu

  DOI：10.1021/jo982319w

  日期：1999.4.1

  The A/B and the C/D/E rings of the xestobergsterol skeleton have been stereoselectively synthesized starting with testosterone and epiandrosterone, respectively. A deconjugative ketalization of the A-ring enone of testosterone provided a handle for functionalization of the B-ring. A stereoselective aldol condensation was used to incorporate the E-ring.