1-O-hexadecyl-2-O-palmitoyl-3-O-phosphoryl-sn-glycerol

• 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: 1-O-hexadecyl-2-O-palmitoyl-3-O-phosphoryl-sn-glycerol
• 英文别名: 1-Hexadecyl-2-hexadecanoyl-glycero-3-phosphate；[(2R)-1-hexadecoxy-3-phosphonooxypropan-2-yl] hexadecanoate
• 化学式: C₃₅H₇₁O₇P
• 分子量: 634.918
• InChiKey: VHSFYIPCRZJPED-UUWRZZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.3
• 重原子数：
  43
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-十六烷醇 在 palladium on activated charcoal 4-二甲氨基吡啶 、 三氟化硼乙醚 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 1-O-hexadecyl-2-O-palmitoyl-3-O-phosphoryl-sn-glycerol
  参考文献：
  名称：

  Efficient Synthesis of Phospholipids from Glycidyl Phosphates

  摘要：

  New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O-palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.

  DOI：

  10.1021/jo010734+

文献信息

• Efficient Synthesis of Phospholipids from Glycidyl Phosphates
  作者：Jan Lindberg、Johan Ekeroth、Peter Konradsson

  DOI：10.1021/jo010734+

  日期：2002.1.1

  New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O-palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.