apoptolidin hexaacetate | 476487-95-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: apoptolidin hexaacetate
• 英文别名: [(2S,4S,5S,8E,10E,12R,13R,14E,16E,18E)-2-[(R)-acetyloxy-[(2R,3R,4S,5S,6R)-4-acetyloxy-6-[(2R)-2-[(2R,4S,5S,6S)-5-[(2S,4R,5R,6R)-5-acetyloxy-4-methoxy-6-methyloxan-2-yl]oxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-3-methoxypropyl]-2-hydroxy-3,5-dimethyloxan-2-yl]methyl]-12-[(2R,3S,4R,5S,6S)-3,4-diacetyloxy-5-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-9,13,15,17,19-pentamethyl-20-oxo-1-oxacycloicosa-8,10,14,16,18-pentaen-5-yl] acetate
• CAS: 476487-95-3
• 化学式: C₇₀H₁₀₈O₂₇
• 分子量: 1381.61
• InChiKey: MWFPBJODLXQNMA-ZGQVSNDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  97
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  326
• 氢给体数：
  2
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  apoptolidin hexaacetate 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 [(2S,4S,5S,8E,10E,12R,13R,14E,16E,18E)-2-[(R)-acetyloxy-[(2R,3R,4S,5S,6R)-4-acetyloxy-6-[(2R)-2-acetyloxy-3-methoxypropyl]-2-hydroxy-3,5-dimethyloxan-2-yl]methyl]-12-[(2R,3S,4R,5S,6S)-3,4-diacetyloxy-5-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-9,13,15,17,19-pentamethyl-20-oxo-1-oxacycloicosa-8,10,14,16,18-pentaen-5-yl] acetate
  参考文献：
  名称：

  Toward a Stable Apoptolidin Derivative:  Identification of Isoapoptolidin and Selective Deglycosylation of Apoptolidin

  摘要：

  graphicIsoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.

  DOI：

  10.1021/ol026829v
• 作为产物：
  描述：

  (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 、 alkaline earth salt of/the/ methylsulfuric acid 以38%的产率得到apoptolidin hexaacetate
  参考文献：
  名称：

  Toward a Stable Apoptolidin Derivative:  Identification of Isoapoptolidin and Selective Deglycosylation of Apoptolidin

  摘要：

  graphicIsoapoptolidin was isolated from crude fermentation extracts of the apoptolidin-producing microorganism Nocardiopsis sp. Apoptolidin isomerizes to isoapoptolidin upon treatment with methanolic triethylamine to establish a 1.4:1 equilibrium mixture of isoapoptolidin and apoptolidin. Semisynthesis of a peracetylated and deglycosylated derivative of apoptolidin is also described.

  DOI：

  10.1021/ol026829v