O-benzyl O-[(S)-2-(benzyloxycarbonyl)-2-(benzyloxycarbonylamino)ethyl] O-[1,2-di-(O-palmitoyl)-sn-glycer-3-yl] phosphate | 1240407-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: O-benzyl O-[(S)-2-(benzyloxycarbonyl)-2-(benzyloxycarbonylamino)ethyl] O-[1,2-di-(O-palmitoyl)-sn-glycer-3-yl] phosphate
• CAS: 1240407-85-5
• 化学式: C₆₀H₉₂NO₁₂P
• 分子量: 1050.36
• InChiKey: GWXRAYFRFNWHBY-WSZONITJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  74.0
• 可旋转键数：
  46.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  161.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  O-benzyl O-[(S)-2-(benzyloxycarbonyl)-2-(benzyloxycarbonylamino)ethyl] O-[1,2-di-(O-palmitoyl)-sn-glycer-3-yl] phosphate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以95%的产率得到dipalmitoylphosphatidyl-L-serine
  参考文献：
  名称：

  Optimized synthesis of phosphatidylserine

  摘要：

  The synthesis of phosphatidyl serine containing saturated fatty acids was thoroughly studied and optimized in order to establish a protocol amenable to large-scale synthesis. The key step was a one-pot multicomponent reaction involving an O-benzyl phosphorodiamidite, protected serine and diacylglycerol, followed by in situ oxidation of the resulting phosphite. In order to replace expensive and poorly stable tetrazole, a screening of substitutes was carried out and imidazolium chloride was selected as the best suited one.

  DOI：

  10.1007/s00726-009-0447-0
• 作为产物：
  描述：

  在 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以5.431 g的产率得到O-benzyl O-[(S)-2-(benzyloxycarbonyl)-2-(benzyloxycarbonylamino)ethyl] O-[1,2-di-(O-palmitoyl)-sn-glycer-3-yl] phosphate
  参考文献：
  名称：

  Optimized synthesis of phosphatidylserine

  摘要：

  The synthesis of phosphatidyl serine containing saturated fatty acids was thoroughly studied and optimized in order to establish a protocol amenable to large-scale synthesis. The key step was a one-pot multicomponent reaction involving an O-benzyl phosphorodiamidite, protected serine and diacylglycerol, followed by in situ oxidation of the resulting phosphite. In order to replace expensive and poorly stable tetrazole, a screening of substitutes was carried out and imidazolium chloride was selected as the best suited one.

  DOI：

  10.1007/s00726-009-0447-0