30-(R)-Dihydrorapamycin | 144006-35-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: 30-(R)-Dihydrorapamycin
• CAS: 144006-35-9
• 化学式: C₅₁H₈₁NO₁₃
• 分子量: 916.203
• InChiKey: ZRWYGDVCYBZEJN-VLKLCEOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  65.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  198.59
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  30-(R)-Dihydrorapamycin 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到
  参考文献：
  名称：

  Manipulation of the Rapamycin Effector Domain. Selective Nucleophilic Substitution of the C7 Methoxy Group

  摘要：

  The C-7 methoxy group in rapamycin has been found to be labile toward acidic reagents. Conditions have been developed to replace this group with a number of different nucleophiles, such as alcohols, thiols, and electron-rich aromatic systems. This novel, efficient transformation allows the selective manipulation of the rapamycin effector domain.

  DOI：

  10.1021/jo00101a006
• 作为产物：
  描述：

  雷帕霉素 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (1R,9S,12S,15R,16E,18R,19S,20S,21R,23S,24E,26E,28E,30S,32S,35R)-1,18,20-trihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14-tetrone 、 30-(R)-Dihydrorapamycin
  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