5'-O-dimethoxytritil-2'-O-methyladenosine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite) | 138906-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-dimethoxytritil-2'-O-methyladenosine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite)
• 英文别名: N(iPr)2P(OCH2CH2CN)(-3)[DMT(-5)]Ribf2Me(b)-adenin-9-yl；3-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-methoxyoxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 138906-75-9
• 化学式: C₄₁H₅₀N₇O₇P
• 分子量: 783.864
• InChiKey: XWBXKGYBWJAXGN-HLHZJIEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-[2-[3,5-Bis[2-[2-(4-bromo-2,3,5,6-tetramethylphenyl)-9-(2,4,6-trimethylphenyl)-1,10-phenanthrolin-3-yl]ethynyl]phenyl]ethynyl]-2-(4-bromo-2,3,5,6-tetramethylphenyl)-9-(2,4,6-trimethylphenyl)-1,10-phenanthroline 、 5'-O-dimethoxytritil-2'-O-methyladenosine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite) 在 benzimidazolium triflate 、 N-甲基吡咯烷酮 、 1-羟基-6-硝基苯并三唑 作用下， 以 乙腈 为溶剂， 反应 0.2h， 生成 Ura-Ribf2Me-P-Cyt-Ribf2Me-P-dThd
  参考文献：
  名称：

  O-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection

  摘要：

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.

  DOI：

  10.1021/ol800911b
• 作为产物：
  描述：

  5'-O-DMT-2'-O-Me-rA^Pac phosphoramidite 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到5'-O-dimethoxytritil-2'-O-methyladenosine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  O-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection

  摘要：

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.

  DOI：

  10.1021/ol800911b

文献信息

• Solid-Phase Synthesis and Screening of Macrocyclic Nucleotide-Hybrid Compounds Targeted to Hepatitis C NS5B
  作者：Michael Smietana、Robert B. Johnson、Q. May Wang、Eric T. Kool

  DOI：10.1002/chem.200305402

  日期：2004.1.5

  potential cyclic hybrid inhibitor compounds targeting hepatitis C virus NS5B enzyme (the replicating polymerase of HCV) was generated by means of the parallel-pool strategy. Screening of the library revealed that cyclic hybrid c(C(OME)EthenodA) was a significant inhibitor of NS5B, with an IC(50) of 40 microM. Preliminary structure-activity studies of this lead compound are described.

  报道了一种在受控孔玻璃上合成环状核苷酸杂合分子的收敛策略。该方法的一个主要优点是对序列和结构变化没有限制，允许掺入修饰的核糖核苷（如 2'-OMe-核糖核苷酸）以及苏氨醇衍生物。该方法允许通过标准亚磷酰胺化学进行全自动组装，并且基于最近公布的用于制备 DNA 系列中环状寡核苷酸的程序 (M. Smietana, ET Kool, Angew. Chem. 2002, 114, 3856-3859 ; Angew. Chem. Int. Ed. Engl. 2002, 41, 3704-3707)。通过平行池策略生成了针对丙型肝炎病毒 NS5B 酶（HCV 的复制聚合酶）的潜在环状杂合抑制剂化合物库。筛选库显示环状杂化 c(C(OME)EthenodA) 是 NS5B 的重要抑制剂，IC(50) 为 40 microM。描述了该先导化合物的初步结构-活性研究。
• 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.