butyl 3-(2-amino-9-((2R,4S,5R)-4-((5-azidopentanoyl)oxy)-5-(((5-azidopentanoyl)oxy)methyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl)benzoate | 1426244-67-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: butyl 3-(2-amino-9-((2R,4S,5R)-4-((5-azidopentanoyl)oxy)-5-(((5-azidopentanoyl)oxy)methyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl)benzoate
• CAS: 1426244-67-8
• 化学式: C₃₁H₃₉N₁₁O₈
• 分子量: 693.72
• InChiKey: WVVCXLHERDHIDU-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  50.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  275.24
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  prop-2-yn-1-yl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate 、 butyl 3-(2-amino-9-((2R,4S,5R)-4-((5-azidopentanoyl)oxy)-5-(((5-azidopentanoyl)oxy)methyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl)benzoate 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 以79%的产率得到butyl 3-[2-amino-9-[(2R,4S,5R)-4-[5-[4-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]triazol-1-yl]pentanoyloxy]-5-[5-[4-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]triazol-1-yl]pentanoyloxymethyl]oxolan-2-yl]-6-oxo-1H-purin-8-yl]benzoate
  参考文献：
  名称：

  Patchy Supramolecules as Versatile Tools To Probe Hydrophobicity in Nanoglobular Systems

  摘要：

  We describe precise supramolecules that enable the evaluation of the effective hydrophobicity of amphiphilic or "patchy" nanoglobular systems. These supramolecules exhibit the lower critical solution temperature phenomenon, which provides a quantitative measure of their effective hydrophobicity. Specifically, two isomeric 8-aryl-2'-deoxyguanosine derivatives with a transposed pair of methylene groups self-assemble into hexadecameric nanoglobular supramolecular G-quadruplexes (SGQ) that show large differences in their transition temperatures as determined by turbidity and differential scanning calorimetry studies. Molecular modeling studies suggested that differential clustering of the hydrophobic patches on the surface is responsible for the striking differences between the two isomeric supramolecules.

  DOI：

  10.1021/ja401373h
• 作为产物：
  描述：

  8-(3-butoxycarbonylphenyl)-2'-deoxyguanosine 在 sodium azide 、 N,N'-二环己基碳二亚胺 、 DPTS 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 butyl 3-(2-amino-9-((2R,4S,5R)-4-((5-azidopentanoyl)oxy)-5-(((5-azidopentanoyl)oxy)methyl)tetrahydrofuran-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl)benzoate
  参考文献：
  名称：

  Patchy Supramolecules as Versatile Tools To Probe Hydrophobicity in Nanoglobular Systems

  摘要：

  We describe precise supramolecules that enable the evaluation of the effective hydrophobicity of amphiphilic or "patchy" nanoglobular systems. These supramolecules exhibit the lower critical solution temperature phenomenon, which provides a quantitative measure of their effective hydrophobicity. Specifically, two isomeric 8-aryl-2'-deoxyguanosine derivatives with a transposed pair of methylene groups self-assemble into hexadecameric nanoglobular supramolecular G-quadruplexes (SGQ) that show large differences in their transition temperatures as determined by turbidity and differential scanning calorimetry studies. Molecular modeling studies suggested that differential clustering of the hydrophobic patches on the surface is responsible for the striking differences between the two isomeric supramolecules.

  DOI：

  10.1021/ja401373h