6-N-((di-n-butylamino)methylene)-2'-deoxyadenosine | 89128-69-8

• 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: 6-N-((di-n-butylamino)methylene)-2'-deoxyadenosine
• 英文别名: 6-N-(N,N-dibutyl)aminomethylene-2'-deoxyadenosine；6-N-[(di-n-butylamino)methylene]-2'-deoxyadenosine；Adenosine, 2'-deoxy-N-[(dibutylamino)methylene]-；N,N-dibutyl-N'-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]methanimidamide
• CAS: 89128-69-8
• 化学式: C₁₉H₃₀N₆O₃
• 分子量: 390.486
• InChiKey: FRXYAMMLXYUEFN-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 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：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-N-((di-n-butylamino)methylene)-2'-deoxyadenosine 在 水 、 1-羟基苯并三唑 作用下， 以 甲醇 为溶剂， 反应 0.2h， 生成 2'-脱氧腺苷
  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 、 2'-脱氧腺苷 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到6-N-((di-n-butylamino)methylene)-2'-deoxyadenosine
  参考文献：
  名称：

  Nucleotide chemistry. 16. Amidine protecting groups for oligonucleotide synthesis

  摘要：

  DOI：

  10.1021/ja00268a052

文献信息

• Nucleotide chemistry. 16. Amidine protecting groups for oligonucleotide synthesis
  作者：Lincoln J. McBride、Ryszard. Kierzek、Serge L. Beaucage、Marvin H. Caruthers

  DOI：10.1021/ja00268a052

  日期：1986.4
• Oligonucleotide Synthesis Involving Deprotection of Amidine-Type Protecting Groups for Nucleobases under Acidic Conditions
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Yudai Nishino、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol100676j

  日期：2010.6.4

  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.