acetic acid 3,4-diacetoxy-5-[2-(3-butylureido)-6-oxo-1,6-dihydropurin-9-yl]-tetrahydro-furan-2-yl methyl ester | 853684-76-1

• 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: acetic acid 3,4-diacetoxy-5-[2-(3-butylureido)-6-oxo-1,6-dihydropurin-9-yl]-tetrahydro-furan-2-yl methyl ester
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-(butylcarbamoylamino)-6-oxo-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 853684-76-1
• 化学式: C₂₁H₂₈N₆O₉
• 分子量: 508.488
• InChiKey: NTZKYRORXGINDJ-NVQRDWNXSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  189
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  acetic acid 3,4-diacetoxy-5-[2-(3-butylureido)-6-oxo-1,6-dihydropurin-9-yl]-tetrahydro-furan-2-yl methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以99%的产率得到1-butyl-3-[9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-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
• 作为产物：
  描述：

  鸟苷 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 acetic acid 3,4-diacetoxy-5-[2-(3-butylureido)-6-oxo-1,6-dihydropurin-9-yl]-tetrahydro-furan-2-yl methyl ester
  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