2-{(S)-2-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-hydroxy-ethyl}-benzoimidazole-1-sulfonic acid dimethylamide | 479198-87-3

• 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-{(S)-2-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-hydroxy-ethyl}-benzoimidazole-1-sulfonic acid dimethylamide
• CAS: 479198-87-3
• 化学式: C₃₃H₄₃N₃O₆SSi
• 分子量: 637.872
• InChiKey: LLEUXUQITUUXPJ-OIFRRMEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  103.12
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 2-{(S)-2-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-hydroxy-ethyl}-benzoimidazole-1-sulfonic acid dimethylamide 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到Methanesulfonic acid (S)-2-[(4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-(1-dimethylsulfamoyl-1H-benzoimidazol-2-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
• 作为产物：
  描述：

  苯并咪唑 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-{(S)-2-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-hydroxy-ethyl}-benzoimidazole-1-sulfonic acid dimethylamide
  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