(3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-10-((2R,3S,4S,5R,6S)-3,4-Dihydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-17-hydroxy-20-hydroxymethyl-18-methoxy-3,5,7,9,13-pentamethyl-oxacycloicosa-3,5,7,11,13-pentaen-2-one | 562106-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-10-((2R,3S,4S,5R,6S)-3,4-Dihydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-17-hydroxy-20-hydroxymethyl-18-methoxy-3,5,7,9,13-pentamethyl-oxacycloicosa-3,5,7,11,13-pentaen-2-one
• 英文别名: (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S)-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-20-(hydroxymethyl)-18-methoxy-3,5,7,9,13-pentamethyl-1-oxacycloicosa-3,5,7,11,13-pentaen-2-one
• CAS: 562106-92-7
• 化学式: C₃₃H₅₂O₁₀
• 分子量: 608.77
• InChiKey: MHGXDHDDXFCFRI-GENWRBAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-10-((2R,3S,4S,5R,6S)-3,4-Dihydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-17-hydroxy-20-hydroxymethyl-18-methoxy-3,5,7,9,13-pentamethyl-oxacycloicosa-3,5,7,11,13-pentaen-2-one 在 三乙胺 作用下， 以 氘代甲醇 为溶剂， 反应 72.0h， 生成 (3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-10-((2R,3S,4S,5R,6S)-3,4-Dihydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-17,20-dihydroxy-18-methoxy-3,5,7,9,13-pentamethyl-oxacyclohenicosa-3,5,7,11,13-pentaen-2-one
  参考文献：
  名称：

  Facile Synthetic Access to and Biological Evaluation of the Macrocyclic Core of Apoptolidin

  摘要：

  [GRAPHICS]Oxidative cleavage of the C-20/C-21 bond in apoptolidin (1) provides two fragments of similar complexity, facilitating a divide-and-diversify strategy for the determination of the structural basis for apoptolidin's biological activity, the remarkably selective induction of apoptosis in sensitive cell lines. The ability of compounds derived from this cleavage to inhibit mitochondrial F0F1-ATPase is reported.

  DOI：

  10.1021/ol0346335
• 作为产物：
  描述：

  (3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-20-Hydroxymethyl-18-methoxy-10-((2R,3S,4R,5S,6S)-5-methoxy-6-methyl-3,4-bis-triethylsilanyloxy-tetrahydro-pyran-2-yloxy)-3,5,7,9,13-pentamethyl-17-triethylsilanyloxy-oxacycloicosa-3,5,7,11,13-pentaen-2-one 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以100%的产率得到(3E,5E,7E,11E,13E)-(9R,10R,17S,18S,20S)-10-((2R,3S,4S,5R,6S)-3,4-Dihydroxy-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-17-hydroxy-20-hydroxymethyl-18-methoxy-3,5,7,9,13-pentamethyl-oxacycloicosa-3,5,7,11,13-pentaen-2-one
  参考文献：
  名称：

  Facile Synthetic Access to and Biological Evaluation of the Macrocyclic Core of Apoptolidin

  摘要：

  [GRAPHICS]Oxidative cleavage of the C-20/C-21 bond in apoptolidin (1) provides two fragments of similar complexity, facilitating a divide-and-diversify strategy for the determination of the structural basis for apoptolidin's biological activity, the remarkably selective induction of apoptosis in sensitive cell lines. The ability of compounds derived from this cleavage to inhibit mitochondrial F0F1-ATPase is reported.

  DOI：

  10.1021/ol0346335