3-O-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol | 637774-41-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-O-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
• 英文别名: 3-O-oleoyl-2-O-(tetrahydro-pyran-2-yloxy)ethyl-sn-glycerol；[(2R)-3-hydroxy-2-[2-(oxan-2-yloxy)ethoxy]propyl] (Z)-octadec-9-enoate
• CAS: 637774-41-5
• 化学式: C₂₈H₅₂O₆
• 分子量: 484.717
• InChiKey: IINSDXZAIBFXAT-RRIZESPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  34
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 三甲基溴硅烷 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 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：

  1-O-(4-methoxybenzyl)-3-O-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以66%的产率得到3-O-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
  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

• Analogs of lysophosphatidic acid and methods of making and using thereof
  申请人：Prestwich D. Glenn

  公开号：US20070123492A1

  公开（公告）日：2007-05-31

  Described herein are analogs of lysophosphatidic acid. Also described herein are methods of making and using analogs of lysophosphatidic acid.

  本文描述了溶血磷脂酸的类似物。本文还描述了制备和使用溶血磷脂酸类似物的方法。
• [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
• Synthesis of Migration-Resistant Hydroxyethoxy Analogues of Lysophosphatidic Acid
  作者：Lian Qian、Yong Xu、Hiroyuki Arai、Junken Aoki、Thomas M. McIntyre、Glenn D. Prestwich

  DOI：10.1021/ol0358758

  日期：2003.11.1

  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.