2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(2-O-methoxycetyl-α-D-mannopyranosyl)glycerol | 1273157-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(2-O-methoxycetyl-α-D-mannopyranosyl)glycerol
• CAS: 1273157-15-5
• 化学式: C₆₀H₁₁₁O₂₄P
• 分子量: 1247.5
• InChiKey: QZLLGHKSMKMLJD-PWBLAMFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  85.0
• 可旋转键数：
  54.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  337.72
• 氢给体数：
  7.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(2-O-methoxycetyl-α-D-mannopyranosyl)glycerol 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 2.75h， 以84%的产率得到2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(α-D-mannopyranosyl)glycerol sodium salt
  参考文献：
  名称：

  A PIM2 analogue suppresses allergic airway disease

  摘要：

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.058
• 作为产物：
  描述：

  2-O-(benzyloxy-1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(3,4,6-tri-O-benzyl-2-O-methoxycetyl-α-D-mannopyranosyl)glycerol 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到2-O-(1,2-di-O-stearoyl-sn-glycero-3-phosphoryl)-1,3-bis-(2-O-methoxycetyl-α-D-mannopyranosyl)glycerol
  参考文献：
  名称：

  A PIM2 analogue suppresses allergic airway disease

  摘要：

  Two approaches for the synthesis of a phosphatidylinositol dimannoside (PIM2) analogue 4 that mimics the suppressive activity of natural PIMs and also synthetic PIM2 have been developed. This analogue, where the inositol core was replaced by glycerol, was tested for its ability to suppress cellular inflammation in a mouse model of allergic asthma and shown to be effective in suppressing airway eosinophilia. Suppression of all inflammatory cells monitored was observed, indicating a general blockade of cellular activity. These data indicate that the inositol core is not essential for this suppressive activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.058