(22R,23R,24S)-22,23-diacetoxy-24-methyl-3α,5-cyclo-5α-cholestan-6-one | 106560-81-0

• 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: (22R,23R,24S)-22,23-diacetoxy-24-methyl-3α,5-cyclo-5α-cholestan-6-one
• CAS: 106560-81-0
• 化学式: C₃₂H₅₀O₅
• 分子量: 514.746
• InChiKey: AHWIQLBLKIPXQT-GAFPOSGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (22R,23R,24S)-22,23-diacetoxy-24-methyl-3α,5-cyclo-5α-cholestan-6-one 在 吡啶溴化氢盐 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 4.0h， 以86%的产率得到(22R,23R,24S)-22,23-diacetoxy-24-methyl-5α-cholest-2-en-6-one
  参考文献：
  名称：

  Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

  摘要：

  The convergent synthesis of biosynthetic precursors of brassinosteroids with a Delta(2)-bond in cycle A-secasterol and 24-episecasterol-was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Delta(22)-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.

  DOI：

  10.1134/s1068162010060117
• 作为产物：
  描述：

  (22R,23R,24S)-22,23-dihydroxy-24-methyl-3α,5-cyclo-5α-cholestan-6-one 、 乙酸酐 在 吡啶 作用下， 反应 6.0h， 以92%的产率得到(22R,23R,24S)-22,23-diacetoxy-24-methyl-3α,5-cyclo-5α-cholestan-6-one
  参考文献：
  名称：

  Synthesis of secasterol and 24-episecasterol and their toxicity for MCF-7 cells

  摘要：

  The convergent synthesis of biosynthetic precursors of brassinosteroids with a Delta(2)-bond in cycle A-secasterol and 24-episecasterol-was performed. The key stages in the construction of the side chain in these compounds were the Julia olefination of the steroid 22-aldehyde followed by the Sharpless asymmetric dihydroxylation of the intermediate Delta(22)-olefin. The cytotoxicity of the synthesized compounds for breast carcinoma MCF-7 cells was assessed.

  DOI：

  10.1134/s1068162010060117