Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-guanin-9-yl | 1228304-71-9

• 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: Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-guanin-9-yl
• 英文别名: [(2R,3R,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 1228304-71-9
• 化学式: C₃₄H₃₁N₅O₈
• 分子量: 637.649
• InChiKey: ZGJRPBMTQUNBCK-BQOYKFDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-[2-(dimethylaminomethylideneamino)-6-oxo-1H-purin-9-yl]-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate 在 水 、 1-羟基苯并三唑 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-5)]Ribf(b)-guanin-9-yl
  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

文献信息

• 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.