2-(3-chlorophenyl)-N-(2-oxo-2-((2-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)amino)ethyl)acetamide | 857466-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(3-chlorophenyl)-N-(2-oxo-2-((2-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)amino)ethyl)acetamide
• CAS: 857466-16-1
• 化学式: C₄₆H₄₉ClN₂O₈
• 分子量: 793.357
• InChiKey: KEEDPWJQANLDQG-PPWNLENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  57.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  113.58
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(3-chlorophenyl)-N-(2-oxo-2-((2-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)amino)ethyl)acetamide 在 Pd(OH)2/C 、 氢气 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001
• 作为产物：
  描述：

  聚合甲醛 、 3-氯苯乙酸 、 (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2-isocyano-ethoxy)-tetrahydro-pyran 在 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以37%的产率得到2-(3-chlorophenyl)-N-(2-oxo-2-((2-(((2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)ethyl)amino)ethyl)acetamide
  参考文献：
  名称：

  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors

  摘要：

  A library of small molecule heparan sulfate (HS) mimetics was synthesized by employing the Ugi four-component condensation of D-mannopyranoside-derived isocyanides with formaldehyde as the carbonyl component and a selection of carboxylic acids and amines, followed by sulfonation. The library was used to probe the subtle differences surrounding the ionic binding sites of three HS-binding angiogenic growth factors (FGF-1, FGF-2 and VEGF). Each compound features 3 or 4 sulfo groups which serve to anchor the ligand to the HS-binding site of the protein, with a diverse array of functionality in place extending from C-1 or C-6 to probe for adjacent favorable binding interactions. Selectivity of binding to these proteins was clearly observed and supported by molecular docking calculations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.001