6-N-(N,N-dibutylformamidine)adenosine | 1228304-61-7

• 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: 6-N-(N,N-dibutylformamidine)adenosine
• 英文别名: 6-N-(N,N-dibutyl)aminomethyleneadenosine；N,N-dibutyl-N'-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]methanimidamide
• CAS: 1228304-61-7
• 化学式: C₁₉H₃₀N₆O₄
• 分子量: 406.485
• InChiKey: SJDLFOYOVSTGGE-NVQRDWNXSA-N

物化性质

• 沸点：
  650.4±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-N-(N,N-dibutylformamidine)adenosine 在 水 、 1-羟基苯并三唑 作用下， 以 甲醇 为溶剂， 反应 0.3h， 生成 腺苷
  参考文献：
  名称：

  Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions

  摘要：

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.

  DOI：

  10.1021/ol100676j
• 作为产物：
  描述：

  N,N-dibutylformamide dimethyl acetal 、 腺苷 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到6-N-(N,N-dibutylformamidine)adenosine
  参考文献：
  名称：

  Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions

  摘要：

  Amidine-type protecting groups, i.e., N,N-dimethylformamidine (dmf) and N,N-dibutylformamidine (dbf) groups, introduced Into nucleobases were rapidly removed under mild acidic conditions using imidazolium triflate (IMT) or 1-hydroxybenztriazole (HOBt). This new deprotection strategy allowed a 2'-O-methyl-RNA derivative bearing a base-labile group to be efficiently synthesized using a silyl-type linker. It was also found that our new method could be applied to the synthesis of an unmodified RNA oligomer.

  DOI：

  10.1021/ol100676j