C2'O-C3'O-C16O-C23O-C4'''O-penta(triethylsilyl)apoptolidin | 502156-13-0

• 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: C2'O-C3'O-C16O-C23O-C4'''O-penta(triethylsilyl)apoptolidin
• CAS: 502156-13-0
• 化学式: C₈₈H₁₆₆O₂₁Si₅
• 分子量: 1700.7
• InChiKey: DRVVYGGLJSUKMF-DBLZWSBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.73
• 重原子数：
  114.0
• 可旋转键数：
  40.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  234.67
• 氢给体数：
  3.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  C2'O-C3'O-C16O-C23O-C4'''O-penta(triethylsilyl)apoptolidin 在 lead(IV) acetate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 以87%的产率得到(3R,4S,5S,6R)-6-{(R)-2-[(2R,4S,5S,6S)-4-Hydroxy-5-((2S,4R,5R,6R)-4-methoxy-6-methyl-5-triethylsilanyloxy-tetrahydro-pyran-2-yloxy)-4,6-dimethyl-tetrahydro-pyran-2-yloxy]-3-methoxy-propyl}-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-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：

  三乙基硅基三氟甲磺酸酯 、 (8E,10E,12R,13R,14E,16E,18E)-12-羟基-13-甲基-20-氧代氧杂环二十-8,10,14,16,18-五烯-2,4,5-三基 在 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以65%的产率得到C2'O-C3'O-C16O-C23O-C4'''O-penta(triethylsilyl)apoptolidin
  参考文献：
  名称：

  Toward a Structure−Activity Relationship for Apoptolidin:  Selective Functionalization of the Hydroxyl Group Array

  摘要：

  [GRAPHICS]To investigate the structural basis for the exceptional selectivity and activity of apoptolidin (1), a strategy has been devised that allows for selective functionalization of seven of its eight hydroxyl groups based on progressive silyl protection, derivatization, and deprotection. The syntheses of these derivatives and their ability to inhibit F0F1-ATPase are reported.

  DOI：

  10.1021/ol027366w