2-(5-O-tert-butyl-diphenylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-methanesulfonyl-pentitol-1-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole | 479198-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(5-O-tert-butyl-diphenylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-methanesulfonyl-pentitol-1-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole
• CAS: 479198-90-8
• 化学式: C₃₄H₄₅N₃O₈S₂Si
• 分子量: 715.964
• InChiKey: MCUSWXIPULGYJP-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  126.26
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(5-O-tert-butyl-diphenylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-methanesulfonyl-pentitol-1-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole 在 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到2-(5'-O-tert-butyl-diphenyl-2'-deoxy-α-D-ribofuranosyl-1')-1-(N,N-dimethylsulfamoyl)-benzimidazole
  参考文献：
  名称：

  Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-C-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase

  摘要：

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.

  DOI：

  10.1021/ol026609h
• 作为产物：
  描述：

  N,N-二甲基苯并咪唑-1-磺酰胺 在 4-二甲氨基吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 2-(5-O-tert-butyl-diphenylsilyl-2-deoxy-3,4-O-isopropylidene-1-O-methanesulfonyl-pentitol-1-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole
  参考文献：
  名称：

  Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-C-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase

  摘要：

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.

  DOI：

  10.1021/ol026609h