1-butyl-3-[9-(6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-urea | 873795-49-4

• 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: 1-butyl-3-[9-(6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-urea
• CAS: 873795-49-4
• 化学式: C₁₈H₂₆N₆O₆
• 分子量: 422.441
• InChiKey: ZSGVDXYSZXSRBR-SDBHATRESA-N

物化性质

• 熔点：
  177-179 °C(Solv: chloroform (67-66-3))
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152.62
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-butyl-3-[9-(6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-urea 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition

  摘要：

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.

  DOI：

  10.1021/ja0545517
• 作为产物：
  描述：

  2',3',5'-三乙酰鸟苷 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.0h， 生成 1-butyl-3-[9-(6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-urea
  参考文献：
  名称：

  A Quadruply Hydrogen Bonded Heterocomplex Displaying High-Fidelity Recognition

  摘要：

  An exceptionally strong quadruply hydrogen-bonded complex is formed between 2,7-diamido-1,8-naphthyridine 3 (DAN) and the butylurea of guanosine 6 (UG) in chloroform. The UG unit can be prepared in four steps from guanosine on a 10 g scale in excellent yields without chromatographic purification. The association constant (K-assoc approximate to 5 x 10(7) m(-1)) for the UG(.)DAN complex determined by fluorescence energy transfer from the naphthyridine unit of 3 to coumarin 343 covalently linked UG (18) is among the highest reported for a neutral DNA base-pair analogue. The weak self-association of DAN (K-dimer < 10 m(-1)) and UG (K-dimer ca. 200-300 m(-1)) means that the UG-DAN complex forms with unparalleled fidelity.

  DOI：

  10.1021/ja0545517