| 158472-52-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 158472-52-7
• 化学式: C₄₇H₈₀O₁₁
• 分子量: 821.146
• InChiKey: VZOBMTCTQBDBAH-VOFYMKDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  58.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  150.21
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  在 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Studies on selective reductions of rapamycin

  摘要：

  The reaction of rapamycin (1) with different reductive agents has been studied. As expected, the C-14 ketone of the ''tricarbonyl'' unit is the most electrophilic center in the molecule and could be selectively converted to either the alcohol (Zn/AcOH or DIBAL) or to the C-14 methylene (H2S, pyridine/MeOH). Under Luche's conditions, the C-14 carbonyl was protected and reduction took place stereoselectively at both C-24 and C-30 (NaBH4/CeCl3) or exclusively at C-30 (NaBH3CN/CeCl3). Selective reaction at C-30 also took place under Evans conditions with NaBH(OAc)(3). These reactions allow the selective manipulation of the rapamycin ''effector domain''.

  DOI：

  10.1016/s0040-4039(00)78248-7
• 作为产物：
  描述：

  雷帕霉素 在 sodium tetrahydroborate 、 cerium(III) chloride 、 dowex 、 氰化四丁基铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 7.25h， 生成
  参考文献：
  名称：

  Studies on selective reductions of rapamycin

  摘要：

  The reaction of rapamycin (1) with different reductive agents has been studied. As expected, the C-14 ketone of the ''tricarbonyl'' unit is the most electrophilic center in the molecule and could be selectively converted to either the alcohol (Zn/AcOH or DIBAL) or to the C-14 methylene (H2S, pyridine/MeOH). Under Luche's conditions, the C-14 carbonyl was protected and reduction took place stereoselectively at both C-24 and C-30 (NaBH4/CeCl3) or exclusively at C-30 (NaBH3CN/CeCl3). Selective reaction at C-30 also took place under Evans conditions with NaBH(OAc)(3). These reactions allow the selective manipulation of the rapamycin ''effector domain''.

  DOI：

  10.1016/s0040-4039(00)78248-7