2-[(2R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-benzoimidazole-1-sulfonic acid dimethylamide | 479198-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(2R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-benzoimidazole-1-sulfonic acid dimethylamide
• CAS: 479198-94-2
• 化学式: C₃₀H₃₇N₃O₅SSi
• 分子量: 579.792
• InChiKey: PGCQXYXFYWFGBB-UPRLRBBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  93.89
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[(2R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-benzoimidazole-1-sulfonic acid dimethylamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2-(2'-deoxy-β-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：

  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 在 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到2-[(2R,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-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