(3α,8α,9β,10α,13α,14β,17α,20S)-chol-5-en-24-oic acid methyl ester | 548459-78-5

• 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)-chol-5-en-24-oic acid methyl ester
• 英文别名: ent-chol-5-en-3-ol
• CAS: 548459-78-5
• 化学式: C₂₅H₄₀O₃
• 分子量: 388.591
• InChiKey: IMNIZYXAQQBADI-ZXXZTTEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3α,8α,9β,10α,13α,14β,17α,20S)-chol-5-en-24-oic acid methyl ester 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 chromium trioxide-pyridine complex 、 Celite 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3α,8α,9β,10α,13α,14β,17β,20S)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}cholesta-5,16,24-trien
  参考文献：
  名称：

  First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

  摘要：

  We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00174-5
• 作为产物：
  描述：

  methyl (3α,8α,9β,10α,13α,14β,20S,22E)-3-(acetyloxy)chola-5,16,22-trien-24-oate 在 platinum on activated charcoal 盐酸 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 60.0 ℃ 、206.84 kPa 条件下， 反应 1.0h， 生成 (3α,8α,9β,10α,13α,14β,17α,20S)-chol-5-en-24-oic acid methyl ester
  参考文献：
  名称：

  First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

  摘要：

  We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00174-5

文献信息

• Synthesis of ent-25-hydroxycholesterol
  作者：Emily J. Westover、Douglas F. Covey

  DOI：10.1016/j.steroids.2006.01.007

  日期：2006.6

  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.