N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine | 1311147-64-4

• 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: N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
• CAS: 1311147-64-4
• 化学式: C₅₀H₆₀N₆O₉Si
• 分子量: 917.147
• InChiKey: NQRYXRVGFOIIJU-YLGHLPMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  66.0
• 可旋转键数：
  18.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  174.38
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-cyanoethyl-(N,N-diisopropylamino)chlorophosphite 、 N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-3'-O-[(2-cyanoethyl)(N,N-diisopropylamino)phosphino]-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
  参考文献：
  名称：

  Nucleobase and Ribose Modifications Control Immunostimulation by a MicroRNA-122-mimetic RNA

  摘要：

  Immune stimulation is a significant hurdle in the development of effective and safe RNA interference therapeutics. Here, we address this problem in the context of a mimic of microRNA-122 by employing novel nucleobase and known 2'-ribose modifications. The nucleobase modifications are analogues of adenosine and guanosine that contain cyclopentyl and propyl minor-groove projections. Via a site-by-site chemical modification analysis, we identify several immunostimulatory 'hot spots' within the miRNA guide strand at which single base modifications significantly reduce immune stimulation. A duplex containing one base modification on each strand proved to be most effective in preventing immune stimulation.

  DOI：

  10.1021/ja202492e
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 silver nitrate 、 N,N-二异丙基乙胺 、 三苯基膦 、 甲胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 2-甲基-2-硝基丙烷 为溶剂， 反应 54.0h， 生成 N2-cyclopentyl-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-O6-(2-(p-nitrophenyl)ethyl)guanosine
  参考文献：
  名称：

  Nucleobase and Ribose Modifications Control Immunostimulation by a MicroRNA-122-mimetic RNA

  摘要：

  Immune stimulation is a significant hurdle in the development of effective and safe RNA interference therapeutics. Here, we address this problem in the context of a mimic of microRNA-122 by employing novel nucleobase and known 2'-ribose modifications. The nucleobase modifications are analogues of adenosine and guanosine that contain cyclopentyl and propyl minor-groove projections. Via a site-by-site chemical modification analysis, we identify several immunostimulatory 'hot spots' within the miRNA guide strand at which single base modifications significantly reduce immune stimulation. A duplex containing one base modification on each strand proved to be most effective in preventing immune stimulation.

  DOI：

  10.1021/ja202492e