Methanesulfonic acid (R)-1-{6-[2-(tert-butoxycarbonyl-methyl-amino)-thiazol-5-yl]-1-dimethylsulfamoyl-1H-benzoimidazol-2-yl}-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester | 479198-88-4

• 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: Methanesulfonic acid (R)-1-{6-[2-(tert-butoxycarbonyl-methyl-amino)-thiazol-5-yl]-1-dimethylsulfamoyl-1H-benzoimidazol-2-yl}-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester
• CAS: 479198-88-4
• 化学式: C₄₃H₅₇N₅O₁₀S₃Si
• 分子量: 928.237
• InChiKey: XUAGWWVKPADZSI-LIVOIKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  62.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  168.69
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-1-{6-[2-(tert-butoxycarbonyl-methyl-amino)-thiazol-5-yl]-1-dimethylsulfamoyl-1H-benzoimidazol-2-yl}-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester 在 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以58%的产率得到(5-{2-[(2S,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-3-dimethylsulfamoyl-3H-benzoimidazol-5-yl}-thiazol-2-yl)-methyl-carbamic acid tert-butyl ester
  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：

  6-(2-N-tert-butoxycarbonyl-N-methyl-aminothiazol-5-yl)-1-(N,N-dimethylsulfamoyl)-benzimidazole 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， 反应 3.25h， 生成 Methanesulfonic acid (R)-1-{6-[2-(tert-butoxycarbonyl-methyl-amino)-thiazol-5-yl]-1-dimethylsulfamoyl-1H-benzoimidazol-2-yl}-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl ester
  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