3-O-dibenzylphosphoryl-1-O-hexadecyl-sn-glycerol | 396091-85-3

• 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: 3-O-dibenzylphosphoryl-1-O-hexadecyl-sn-glycerol
• 英文别名: dibenzyl [(2R)-3-hexadecoxy-2-hydroxypropyl] phosphate
• CAS: 396091-85-3
• 化学式: C₃₃H₅₃O₆P
• 分子量: 576.754
• InChiKey: STNOQTPHCDXOHV-MGBGTMOVSA-N

物化性质

• 沸点：
  659.6±55.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  40
• 可旋转键数：
  26
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-dibenzylphosphoryl-1-O-hexadecyl-sn-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以90%的产率得到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+
• 作为产物：
  描述：

  Phosphorous acid dibenzyl ester (R)-1-oxiranylmethyl ester 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.67h， 生成 3-O-dibenzylphosphoryl-1-O-hexadecyl-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+