{3-[3-Bromomethyl-5-(3-tert-butoxycarbonylmethoxy-benzyloxy)-phenoxymethyl]-phenoxy}-acetic acid tert-butyl ester | 906458-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {3-[3-Bromomethyl-5-(3-tert-butoxycarbonylmethoxy-benzyloxy)-phenoxymethyl]-phenoxy}-acetic acid tert-butyl ester
• CAS: 906458-07-9
• 化学式: C₃₃H₃₉BrO₈
• 分子量: 643.572
• InChiKey: ATMYGLRUVNPQLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {3-[3-Bromomethyl-5-(3-tert-butoxycarbonylmethoxy-benzyloxy)-phenoxymethyl]-phenoxy}-acetic acid tert-butyl ester 在 18-冠醚-6 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氢氧化钾 、 丙酮 为溶剂， 反应 36.0h， 生成 2-[3-[[3-[[3-[[3,5-Bis[[3-(carboxymethoxy)phenyl]methoxy]phenyl]methoxy]-5-(hydroxymethyl)phenoxy]methyl]-5-[[3-(carboxymethoxy)phenyl]methoxy]phenoxy]methyl]phenoxy]acetic acid
  参考文献：
  名称：

  Comparison of Facially Amphiphilic Biaryl Dendrimers with Classical Amphiphilic Ones Using Protein Surface Recognition as the Tool

  摘要：

  Facially amphiphilic biaryl dendrimers are compared with the more classical benzyl ether amphiphilic dendrimers for molecular recognition, using protein binding as the probe. The protein used for the proposed study is chymotrypsin (ChT). A generation-dependent binding affinity was observed with the benzyl ether dendrimers, while the affinities were independent of generation in the case of the biaryl dendrimers. Similarly, although the ligands incorporated in both dendrons are the same, the biaryl dendrimers are able to bind more proteins compared to the benzyl ether dendrimers. For example, G3-dendron of biaryl dendrimer can bind six molecules of chymotrypsin, whereas G3-analogue of benzyl ether dendrimers can bind only three molecules of chymotrypsin. This result is consistent with our hypothesis that the internal layers of the facially amphiphilic biaryl dendrons are solvent-exposed and accessible for recognition. In addition, the systematic size differences in dendrons were also used to gain insights into the substrate selectivity that the enzyme gains upon binding to a ligand scaffold.

  DOI：

  10.1021/ja0622406
• 作为产物：
  描述：

  tert-butyl 2-(3-(hydroxymethyl)phenyloxy)acetate 在 18-冠醚-6 N-溴代丁二酰亚胺(NBS) 、 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 0.5h， 生成 {3-[3-Bromomethyl-5-(3-tert-butoxycarbonylmethoxy-benzyloxy)-phenoxymethyl]-phenoxy}-acetic acid tert-butyl ester
  参考文献：
  名称：

  Comparison of Facially Amphiphilic Biaryl Dendrimers with Classical Amphiphilic Ones Using Protein Surface Recognition as the Tool

  摘要：

  Facially amphiphilic biaryl dendrimers are compared with the more classical benzyl ether amphiphilic dendrimers for molecular recognition, using protein binding as the probe. The protein used for the proposed study is chymotrypsin (ChT). A generation-dependent binding affinity was observed with the benzyl ether dendrimers, while the affinities were independent of generation in the case of the biaryl dendrimers. Similarly, although the ligands incorporated in both dendrons are the same, the biaryl dendrimers are able to bind more proteins compared to the benzyl ether dendrimers. For example, G3-dendron of biaryl dendrimer can bind six molecules of chymotrypsin, whereas G3-analogue of benzyl ether dendrimers can bind only three molecules of chymotrypsin. This result is consistent with our hypothesis that the internal layers of the facially amphiphilic biaryl dendrons are solvent-exposed and accessible for recognition. In addition, the systematic size differences in dendrons were also used to gain insights into the substrate selectivity that the enzyme gains upon binding to a ligand scaffold.

  DOI：

  10.1021/ja0622406