(3R,6S)-3-Methyl-6-[(3E,5E,7E,15E)-(2S,9S,11R,13R,14R,17R,18S,20S,21R)-14,18,20-trihydroxy-22-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12-oxo-docosa-3,5,7,15-tetraenyl]-tetrahydro-pyran-2-one | 158472-51-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,6S)-3-Methyl-6-[(3E,5E,7E,15E)-(2S,9S,11R,13R,14R,17R,18S,20S,21R)-14,18,20-trihydroxy-22-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12-oxo-docosa-3,5,7,15-tetraenyl]-tetrahydro-pyran-2-one
• CAS: 158472-51-6
• 化学式: C₄₃H₇₂O₁₀
• 分子量: 749.039
• InChiKey: WPPCFUBSNYGRBL-BOCHJACSSA-N

物化性质

• 沸点：
  848.3±65.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  53.0
• 可旋转键数：
  22.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  151.98
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (3R,6S)-3-Methyl-6-[(3E,5E,7E,15E)-(2S,9S,11R,13R,14R,17R,18S,20S,21R)-14,18,20-trihydroxy-22-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12-oxo-docosa-3,5,7,15-tetraenyl]-tetrahydro-pyran-2-one 在 dowex 、 氢气 作用下， 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 、 氰化四丁基铵 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 7.25h， 生成 (3R,6S)-3-Methyl-6-[(3E,5E,7E,15E)-(2S,9S,11R,13R,14R,17R,18S,20S,21R)-14,18,20-trihydroxy-22-((1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12-oxo-docosa-3,5,7,15-tetraenyl]-tetrahydro-pyran-2-one
  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