[(2R)-3,3-difluoro-2-hydroxypropyl] dimethyl phosphate | 474329-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: [(2R)-3,3-difluoro-2-hydroxypropyl] dimethyl phosphate
• CAS: 474329-43-6
• 化学式: C₅H₁₁F₂O₅P
• 分子量: 220.11
• InChiKey: IFNYQUFJUFJZRH-SCSAIBSYSA-N

物化性质

• 沸点：
  274.0±40.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  棕榈酸 、 [(2R)-3,3-difluoro-2-hydroxypropyl] dimethyl phosphate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以62 mg的产率得到(2R)-3,3-difluoro-2-palmitoyl-1-phosphopropane dimethyl ester
  参考文献：
  名称：

  Concise Synthesis of Acyl Migration-Blocked 1,1-Difluorinated Analogues of Lysophosphatidic Acid

  摘要：

  Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) is an important phospholipid mediator produced by activated platelets and by ovarian cancer cells. Efforts to understand LPA signaling through G-protein-coupled receptors are hampered by the facile acyl migration that results in equilibration to a mixture of the 1- or 2-acyl species under physiological conditions. We describe a new and efficient route to enantiomerically homogeneous lysophospholipid analogues from D-mannitol 1,2:5,6-bis-ace-tonide to give two 1,1-difluorodeoxy analogues of (2R)-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the labile sn-2 LPA species. The F-19 NMR of diastereotopic fluorines, of the difluoromethyl group shows an unexpected solvent dependence.

  DOI：

  10.1021/jo0203037
• 作为产物：
  描述：

  (2R)-3,3-difluoro-2-[(1-tert-butyl-1,1-dimethylsilyl)oxy]-1-phosphopropane dimethyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 [(2R)-3,3-difluoro-2-hydroxypropyl] dimethyl phosphate
  参考文献：
  名称：

  [EN] ANALOGS OF LYSOPHOSPHATIDIC ACID AND METHODS OF MAKING AND USING THEREOF
  [FR] ANALOGUES D'ACIDE LYSOPHOSPHATIDIQUE ET PROCEDES DE LEUR FABRICATION ET DE LEUR UTILISATION

  摘要：

  公开号：

  WO2004092188A3

文献信息

• [EN] ANALOGS OF LYSOPHOSPHATIDIC ACID AND METHODS OF MAKING AND USING THEREOF<br/>[FR] ANALOGUES D'ACIDE LYSOPHOSPHATIDIQUE ET PROCEDES DE LEUR FABRICATION ET DE LEUR UTILISATION
  申请人：UNIV UTAH RES FOUND

  公开号：WO2004092188A3

  公开（公告）日：2005-04-28
• Concise Synthesis of Acyl Migration-Blocked 1,1-Difluorinated Analogues of Lysophosphatidic Acid
  作者：Yong Xu、Glenn D. Prestwich

  DOI：10.1021/jo0203037

  日期：2002.10.1

  Lysophosphatidic acid (LPA, 1- or 2-acyl-sn-glycerol 3-phosphate) is an important phospholipid mediator produced by activated platelets and by ovarian cancer cells. Efforts to understand LPA signaling through G-protein-coupled receptors are hampered by the facile acyl migration that results in equilibration to a mixture of the 1- or 2-acyl species under physiological conditions. We describe a new and efficient route to enantiomerically homogeneous lysophospholipid analogues from D-mannitol 1,2:5,6-bis-ace-tonide to give two 1,1-difluorodeoxy analogues of (2R)-acyl-sn-glycerol 3-phosphate. These compounds are migration-blocked analogues of the labile sn-2 LPA species. The F-19 NMR of diastereotopic fluorines, of the difluoromethyl group shows an unexpected solvent dependence.