Octadecanoic acid (R)-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-dodecanoyloxy-propyl ester | 228406-22-2

• 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: Octadecanoic acid (R)-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-dodecanoyloxy-propyl ester
• CAS: 228406-22-2
• 化学式: C₄₆H₈₄NO₆P
• 分子量: 778.15
• InChiKey: JFYJVDLSXWVBNU-NAHYCMLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  54.0
• 可旋转键数：
  38.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzyloxymethyl-3,4,5-tri-O-p-methoxybenzyl-D-myo-inositol 、 Octadecanoic acid (R)-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-dodecanoyloxy-propyl ester 在 四氮唑 、 间氯过氧苯甲酸 作用下， 生成 Octadecanoic acid (R)-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-tris-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryloxy}-2-dodecanoyloxy-propyl ester
  参考文献：
  名称：

  The structural requirement of phosphatidylinositols as substrate of phosphatidylinositol 3-kinase

  摘要：

  Synthetic distearate phosphatidylinositol (PI) was not phosphorylated by PI 3-kinase. The fatty acids at glycerol sn-2 must be as short as octanoic acid or less to act as a substrate of PI 3-kinase. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00004-0
• 作为产物：
  描述：

  1-O-stearoyl-3-O-benzyl-sn-glycerol 在 palladium on activated charcoal 四氮唑 、 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Octadecanoic acid (R)-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-dodecanoyloxy-propyl ester
  参考文献：
  名称：

  Phosphorylation of Unnatural Phosphatidylinositols with Phosphatidylinositol 3-Kinase

  摘要：

  Phosphatidylinositol analogs (PIC2PIC18) having a series of saturated fatty acid (C2-C18) at sn-2 position were synthesized and subjected to the phosphorylation reaction with phosphatidylinositol 3-kinase (PI 3-kinase). The reactivity of PIC8 with PI 3-kinase turned out to be comparable to that of natural PI, although PIC18 was not phosphorylated under the same condition. The chirality of sn-2 center was not responsible for the phosphorylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00161-7