3-O-di-tert-butylphosphoryl-1-O-palmitoyl-sn-glycerol | 396091-88-6

• 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-di-tert-butylphosphoryl-1-O-palmitoyl-sn-glycerol
• 英文别名: [(2R)-3-[bis[(2-methylpropan-2-yl)oxy]phosphoryloxy]-2-hydroxypropyl] hexadecanoate
• CAS: 396091-88-6
• 化学式: C₂₇H₅₅O₇P
• 分子量: 522.703
• InChiKey: NRWCINYVILKGAY-XMMPIXPASA-N

物化性质

• 沸点：
  577.4±40.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-O-di-tert-butylphosphoryl-1-O-palmitoyl-sn-glycerol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以100%的产率得到1-棕榈酰基-sn-甘油-3-磷酸钠盐
  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：

  在 棕榈酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.67h， 生成 3-O-di-tert-butylphosphoryl-1-O-palmitoyl-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

• Concise Synthesis of Glycerophospholipids
  作者：Tufan K. Mukhopadhyay、Dirk Trauner

  DOI：10.1021/acs.joc.2c02096

  日期：——

  receptors to activate biological pathways. Untangling the roles of individual glycerophospholipids requires clearly defined molecular species, a challenge that can be best addressed through chemical synthesis. However, glycerophospholipid syntheses are often lengthy due to the contrasting polarities found within these lipids. We now report a general strategy to quickly access glycerophospholipids via opening

  甘油磷脂是细胞膜的主要成分，并提供重要的信号分子。除了塑造膜特性外，有些还与特定受体结合以激活生物途径。阐明单个甘油磷脂的作用需要明确定义的分子种类，这一挑战最好通过化学合成来解决。然而，由于这些脂质中存在相反的极性，甘油磷脂的合成通常很漫长。我们现在报告了一种通过雅各布森 Co(salen) 络合物催化的羧酸与磷酸三酯环氧化物的打开来快速获得甘油磷脂的一般策略。我们表明，该方法可以应用于多种市售脂肪酸、光可切换脂肪酸和其他羧酸，以提供相应的甘油磷酸衍生物。