(2R,3R,4R,5S,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-5-(benzoyloxy)-6-((benzoyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-4-yl)oxy)-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate | 1194331-65-1

• 分子结构分类: 有机化合物
• 英文名称: (2R,3R,4R,5S,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-5-(benzoyloxy)-6-((benzoyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-4-yl)oxy)-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS: 1194331-65-1
• 化学式: C₄₃H₄₀FNO₁₅
• 分子量: 829.787
• InChiKey: KTHMAFYXTOUNNR-NXBUSZETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  60.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  208.52
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-5-(benzoyloxy)-6-((benzoyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-4-yl)oxy)-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate 、 焦磷酸四苄酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到(2R,3R,4R,5S,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-5-(benzoyloxy)-6-((benzoyloxy)methyl)-2-((bis(benzyloxy)phosphoryl)oxy)tetrahydro-2H-pyran-4-yl)oxy)-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  The first chemical synthesis of F-4-GlcAβ(1→3)GlcNAc-UDP with the potential of novel substrate and enzyme inhibitor for hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of F-4-GlcA beta(1 -> 3)GlcNAc-UDP is described here. This compound can serve as a novel substrate to study the catalytic mechanism of hyaluronic acid synthases (HASs) and has potential to be donor for these enzymes that extend HA chain at the reducing end. Moreover, it may also behave as inhibitor for the enzymes that act on non-reducing end in the assembly of HA chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.017
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到(2R,3R,4R,5S,6R)-2-(((2R,3R,4R,5S,6R)-3-acetamido-5-(benzoyloxy)-6-((benzoyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-4-yl)oxy)-5-fluoro-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl dibenzoate
  参考文献：
  名称：

  The first chemical synthesis of F-4-GlcAβ(1→3)GlcNAc-UDP with the potential of novel substrate and enzyme inhibitor for hyaluronic acid synthases (HASs)

  摘要：

  The first chemical synthesis of F-4-GlcA beta(1 -> 3)GlcNAc-UDP is described here. This compound can serve as a novel substrate to study the catalytic mechanism of hyaluronic acid synthases (HASs) and has potential to be donor for these enzymes that extend HA chain at the reducing end. Moreover, it may also behave as inhibitor for the enzymes that act on non-reducing end in the assembly of HA chain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.017