Hexadecanoic acid (R)-3-phosphonooxy-2-(tetrahydro-pyran-2-yloxy)-propyl ester | 786704-20-9

• 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: Hexadecanoic acid (R)-3-phosphonooxy-2-(tetrahydro-pyran-2-yloxy)-propyl ester
• 英文别名: [(2R)-2-(oxan-2-yloxy)-3-phosphonooxypropyl] hexadecanoate
• CAS: 786704-20-9
• 化学式: C₂₄H₄₇O₈P
• 分子量: 494.606
• InChiKey: ZNICUEKMTWVXKL-LETIRJCYSA-N

物化性质

• 沸点：
  617.3±65.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (R)-3-phosphonooxy-2-(tetrahydro-pyran-2-yloxy)-propyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以86%的产率得到1-棕榈酰基-sn-甘油-3-磷酸钠盐
  参考文献：
  名称：

  A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

  摘要：

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.161
• 作为产物：
  描述：

  1-palmitoyl-2-(tetrahydropyran-2-yl)-sn-glycerol 在 四氮唑 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 64.0h， 生成 Hexadecanoic acid (R)-3-phosphonooxy-2-(tetrahydro-pyran-2-yloxy)-propyl ester
  参考文献：
  名称：

  A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

  摘要：

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.161

文献信息

• A new approach to the synthesis of lysophospholipids: preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate
  作者：Renato Rosseto、Niloufar Bibak、Joseph Hajdu

  DOI：10.1016/j.tetlet.2004.07.161

  日期：2004.9

  A new stereospecific synthesis of lysophosphatidic acid and lysophosphatidylcholine is reported. The sequence relies on p-nitrophenyl-D-glycerate as a chiral synthon, including chemoselective reduction of the active ester function without affecting other carboxylic ester groups present in the molecule. (C) 2004 Elsevier Ltd. All rights reserved.