(R)-15-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-15-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentadecanoic acid (S)-1-carboxy-ethyl ester | 632323-70-7

• 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: (R)-15-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-15-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentadecanoic acid (S)-1-carboxy-ethyl ester
• CAS: 632323-70-7
• 化学式: C₅₅H₁₀₈O₁₀Si₃
• 分子量: 1013.71
• InChiKey: ORWSRXXGYLUONG-JFVZKXELSA-N

物化性质

• 沸点：
  845.5±65.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.66
• 重原子数：
  68.0
• 可旋转键数：
  34.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  126.82
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (R)-15-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-15-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentadecanoic acid (S)-1-carboxy-ethyl ester 在 lithium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 8.25h， 生成
  参考文献：
  名称：

  Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction

  摘要：

  In addition to two expected pyrazin derivatives, two imidazole analogues of squamocin I have been semisynthetised from squamocin derived alpha-ketoesters/alpha-ketoacid, via an unusual condensation-oxidative decarboxylation reaction with 1,2 diamines in presence of acetic acid and oxygen as the key step. Some of these analogues exhibited potent, although significantly reduced cytotoxicities relatively to squamocin 1. In addition, benzimidazole 8 possessed in comparison with the natural acetogenin some interesting cell cycle effects. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00306-7
• 作为产物：
  描述：

  (S)-3-[(R)-13-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-(tert-butyl-dimethyl-silanyloxy)-tridecyl]-5-methyl-5H-furan-2-one 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以86%的产率得到(R)-15-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-15-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentadecanoic acid (S)-1-carboxy-ethyl ester
  参考文献：
  名称：

  Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction

  摘要：

  In addition to two expected pyrazin derivatives, two imidazole analogues of squamocin I have been semisynthetised from squamocin derived alpha-ketoesters/alpha-ketoacid, via an unusual condensation-oxidative decarboxylation reaction with 1,2 diamines in presence of acetic acid and oxygen as the key step. Some of these analogues exhibited potent, although significantly reduced cytotoxicities relatively to squamocin 1. In addition, benzimidazole 8 possessed in comparison with the natural acetogenin some interesting cell cycle effects. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00306-7