3-(十六烷氧基)-2-羟基丙基二氢磷酸酯 | 52603-03-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 3-(十六烷氧基)-2-羟基丙基二氢磷酸酯
• 英文名称: 1-O-hexadecyl-3-O-phosphoryl-sn-glycerol
• 英文别名: 1-Hexadecyl Lysophosphatidic Acid；[(2R)-3-hexadecoxy-2-hydroxypropyl] dihydrogen phosphate
• CAS: 52603-03-9
• 化学式: C₁₉H₄₁O₆P
• 分子量: 396.505
• InChiKey: XLVRFPVHQPHXAA-LJQANCHMSA-N

物化性质

• 溶解度：
  DMF：5 mg/ml； DMSO：20 mg/ml；乙醇：20 mg/ml；乙醇:PBS (pH 7.2)(1:1): 0.5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-十六烷醇 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 12.0h， 生成 3-(十六烷氧基)-2-羟基丙基二氢磷酸酯
  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

• LIPID DERIVATIVES OF PHOSPHONOACIDS FOR LIPOSOMAL INCORPORATION AND METHOD OF USE
  申请人：Chimerix, Inc.

  公开号：EP0674646B1

  公开（公告）日：2001-10-04
• 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.