3α,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether | 219903-26-1

• 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,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether
• 英文别名: (1S,2R,5R,7R,8R,10S,11S,14R,15S)-14-[(2S)-3-(benzenesulfonyl)-6-methylhept-5-en-2-yl]-8-methoxy-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecane
• CAS: 219903-26-1
• 化学式: C₃₄H₅₀O₃S
• 分子量: 538.835
• InChiKey: MNEGVNSFXXFASV-GLFHUXAFSA-N

物化性质

• 沸点：
  631.8±47.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether 在 乙醇 、 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以74%的产率得到3α,5-cyclo-5α-cholest-24-en-6β-ol 6-methyl ether
  参考文献：
  名称：

  Efficient, Stereoselective Synthesis of 24(S),25-Epoxycholesterol

  摘要：

  Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXR alpha nuclear receptor.

  DOI：

  10.1021/jo981753v
• 作为产物：
  描述：

  (3alpha,5R,6beta,20S)-6-甲氧基-3,5-环孕烷-30-甲醇4-甲基苯磺酸酯 在 正丁基锂 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 正戊烷 为溶剂， 反应 3.0h， 生成 3α,5-cyclo-5α-cholest-24-en-22-phenylsulfonyl-6β-ol 6-methyl ether
  参考文献：
  名称：

  Efficient, Stereoselective Synthesis of 24(S),25-Epoxycholesterol

  摘要：

  Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXR alpha nuclear receptor.

  DOI：

  10.1021/jo981753v

文献信息

• Efficient, Stereoselective Synthesis of 24(<i>S</i>),25-Epoxycholesterol
  作者：Nicholas C. O. Tomkinson、Timothy M. Willson、Jonathon S. Russel、Thomas A. Spencer

  DOI：10.1021/jo981753v

  日期：1998.12.1

  Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXR alpha nuclear receptor.