(3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-ol tosylate | 915159-29-4

• 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: (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-ol tosylate
• CAS: 915159-29-4
• 化学式: C₃₇H₆₀O₄SSi
• 分子量: 629.033
• InChiKey: NJWJXVUZGOLYII-CUNGNIDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-ol tosylate 以 四氢呋喃 、 乙醚 、 二甲基亚砜 为溶剂， 反应 9.83h， 生成 (3α,8α,9β,10α,13α,14β,17α,20S)-25-hydroxycholesterol
  参考文献：
  名称：

  Synthesis of ent-25-hydroxycholesterol

  摘要：

  25-Hydroxycholesterol (25-HC) appears to play a role in several important biological processes, including regulating cellular cholesterol levels and promoting apoptosis. However, in most cases the mechanisms by which 25-HC elicits its biological effects are not known. Insights into mechanisms of 25-HC action can be gained by studying the activity of its enantiomer (ent-25-HC). ent-25-HC is physically and chemically identical to 25-HC; however, 25-HC and ent-25-HC can be distinguished in chiral environments, like a protein binding site. In order to probe the mechanisms of 25-HC action, we have synthesized the enantiomer of 25-HC (ent-25-HC). (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.007
• 作为产物：
  描述：

  (S)-4-[(3R,8R,9R,10S,13S,14R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 48.5h， 生成 (3α,8α,9β,10α,13α,14β,17α,20S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]chol-5-en-24-ol tosylate
  参考文献：
  名称：

  Synthesis of ent-25-hydroxycholesterol

  摘要：

  25-Hydroxycholesterol (25-HC) appears to play a role in several important biological processes, including regulating cellular cholesterol levels and promoting apoptosis. However, in most cases the mechanisms by which 25-HC elicits its biological effects are not known. Insights into mechanisms of 25-HC action can be gained by studying the activity of its enantiomer (ent-25-HC). ent-25-HC is physically and chemically identical to 25-HC; however, 25-HC and ent-25-HC can be distinguished in chiral environments, like a protein binding site. In order to probe the mechanisms of 25-HC action, we have synthesized the enantiomer of 25-HC (ent-25-HC). (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.01.007