sodium 3-O-stearoyl-4,5-di-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-D-myo-inositol | 1228177-03-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: sodium 3-O-stearoyl-4,5-di-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-D-myo-inositol
• CAS: 1228177-03-4
• 化学式: C₁₄₅H₂₀₀O₂₄P*Na
• 分子量: 2381.13
• InChiKey: AUDIQUPHYXXOFR-BEYBTJPPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  30.36
• 重原子数：
  171.0
• 可旋转键数：
  93.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  266.71
• 氢给体数：
  0.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  sodium 3-O-stearoyl-4,5-di-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-D-myo-inositol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 48.25h， 以87%的产率得到sodium 3-O-stearoyl-2,6-di-O-α-D-mannopyranosyl-1-O-(1,2-di-O-stearoyl-sn-glyceryl-3-phosphoryl)-D-myo-inositol
  参考文献：
  名称：

  Synthesis of Mycobacterial Triacylated Phosphatidylinositol Dimannoside Containing an Acyl Lipid Chain at 3-O of Inositol

  摘要：

  A seven-step synthesis of triacylated phosphatidylinositol dimannoside is described from myo-inositol 1,3,5-orthoformate. It proceeded in 31% overall yield via a highly regioselective and stereoselective 2,6-di-O-D-mannosylation as the key step.

  DOI：

  10.1021/ol1008137
• 作为产物：
  描述：

  triethylammonium 3-O-stearoyl-4,5-di-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-D-myo-inositol 在 Dowex 50 W x Na(+) IR-resin 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.0h， 以46 mg的产率得到sodium 3-O-stearoyl-4,5-di-O-benzyl-2,6-di-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-D-myo-inositol
  参考文献：
  名称：

  Synthesis of Mycobacterial Triacylated Phosphatidylinositol Dimannoside Containing an Acyl Lipid Chain at 3-O of Inositol

  摘要：

  A seven-step synthesis of triacylated phosphatidylinositol dimannoside is described from myo-inositol 1,3,5-orthoformate. It proceeded in 31% overall yield via a highly regioselective and stereoselective 2,6-di-O-D-mannosylation as the key step.

  DOI：

  10.1021/ol1008137