Phosphoric acid (S)-2-hydroxy-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-propyl ester dimethyl ester | 637774-51-7

• 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: Phosphoric acid (S)-2-hydroxy-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-propyl ester dimethyl ester
• CAS: 637774-51-7
• 化学式: C₁₂H₂₅O₈P
• 分子量: 328.299
• InChiKey: JWEFDPQNWLTMQX-PXYINDEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  21.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid (S)-2-hydroxy-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-propyl ester dimethyl ester 在 4-二甲氨基吡啶 、 三甲基溴硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

  摘要：

  The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fall to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA.

  DOI：

  10.1021/ol0358758
• 作为产物：
  描述：

  3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-2-O-tert-butyldimethylsilyl-1-O-dimethoxyphosphoryl-sn-glycerol 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到Phosphoric acid (S)-2-hydroxy-3-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-propyl ester dimethyl ester
  参考文献：
  名称：

  Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid

  摘要：

  The susceptibility of lysophosphatidic acid (LPA) to intramolecular acyl migration impedes the determination of specific receptor activation by the sn-1 and sn-2 LPA regioisomers. An efficient enantioselective synthesis of hydroxyethoxy (HE)-substituted analogues of sn-1-acyl and 2-acyl LPA derivatives that possess palmitoyl and oleoyl chains is described. While the palmitoyl derivatives fall to activate calcium release in cells transfected with LPA(2) or LPA(3) G-protein-coupled receptors, the LPA(3) receptor is activated by both 1-HE and 2-HE oleoyl LPA analogues with a potency 10-fold lower than that of the parent oleoyl LPA.

  DOI：

  10.1021/ol0358758

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