1,2-di-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol | 637774-48-2

• 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: 1,2-di-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
• 英文别名: 1,2-di-O-tert-butyl-dimethylsilyl-3-O-(tetrahydro-pyran-2-yloxy)ethyl-sn-glycerol；1,2-di-O-tert-butyl-dimethysilyl-3-O-(tetrahydro-pyran-2-yloxy)ethyl-sn-glycerol；tert-butyl-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-3-[2-(oxan-2-yloxy)ethoxy]propan-2-yl]oxy-dimethylsilane
• CAS: 637774-48-2
• 化学式: C₂₂H₄₈O₅Si₂
• 分子量: 448.791
• InChiKey: MSHPADCDXAWRBX-XJDOXCRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-di-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以58%的产率得到2-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
  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：

  2-(四氢-2H-吡喃-2-氧基)乙醇 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1,2-di-O-tert-butyldimethylsilyl-3-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
  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

• 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.