24(S),25-Epoxycholest-5-en-3β-ol-7-one, 3β-Acetate | 306288-48-2

• 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: 24(S),25-Epoxycholest-5-en-3β-ol-7-one, 3β-Acetate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-7-oxo-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 306288-48-2
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: YSOGDXRTLWYJBU-KLXREMKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  24(S),25-Epoxycholest-5-en-3β-ol-7-one, 3β-Acetate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以71%的产率得到(24S)-24,25-epoxycholest-5-ene-3β,7α-diol 3-acetate
  参考文献：
  名称：

  Synthesis of 7α-hydroxy derivatives of regulatory oxysterols

  摘要：

  7 alpha-Hydroxy derivatives of oxysterols are of considerable interest because of their possible involvement in regulation of cholesterol metabolism This paper describes stereoselective syntheses and complete characterization of the 7 alpha-hydroxy derivatives of four key oxysterols: 25-hydroxycholesterol, 27-hydroxycholesterol, 24(S)-hydroxycholesterol, and 24(S),25-epoxycholesterol. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00131-8
• 作为产物：
  描述：

  (24S)-24,25-epoxycholesteryl acetate 在 叔丁基过氧化氢 、 copper(l) iodide 作用下， 以 癸烷 、 乙腈 为溶剂， 反应 25.0h， 生成 24(S),25-Epoxycholest-5-en-3β-ol-7-one, 3β-Acetate
  参考文献：
  名称：

  Synthesis of 7α-hydroxy derivatives of regulatory oxysterols

  摘要：

  7 alpha-Hydroxy derivatives of oxysterols are of considerable interest because of their possible involvement in regulation of cholesterol metabolism This paper describes stereoselective syntheses and complete characterization of the 7 alpha-hydroxy derivatives of four key oxysterols: 25-hydroxycholesterol, 27-hydroxycholesterol, 24(S)-hydroxycholesterol, and 24(S),25-epoxycholesterol. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00131-8

文献信息

• Stereocontrolled syntheses of 24(S),25-epoxycholesterol and related oxysterols for studies on the activation of LXR receptors
  作者：E.J. Corey、Michael J. Grogan

  DOI：10.1016/s0040-4039(98)02181-9

  日期：1998.12

  Efficient syntheses are described of desmosterol (4), the corresponding 24(S),25 epoxide (6) and various analogs of 6 for evaluation as ligands and functional activators of LXR receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.