2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(4-fluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose | 304436-48-4

• 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: 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(4-fluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose
• 英文别名: (2R,3R,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-(4-fluorobenzimidazol-1-yl)oxolan-3-ol
• CAS: 304436-48-4
• 化学式: C₃₉H₄₅FN₂O₆Si
• 分子量: 684.88
• InChiKey: LBIKBVZXZWQUIZ-UMHCDNJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(4-fluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose 在 N-甲基咪唑 、 2,4,6-三甲基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以52.3%的产率得到2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(4-fluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose 3-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis of Fluorobenzene and Benzimidazole Nucleic-Acid Analogues and Their Influence on Stability of RNA Duplexes

  摘要：

  Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T-m differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene . fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ... H H-bond.

  DOI：

  10.1002/1522-2675(20000809)83:8<1791::aid-hlca1791>3.0.co;2-k
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 26.5h， 生成 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(4-fluoro-1H-benzimidazol-1-yl)-β-D-ribofuranose
  参考文献：
  名称：

  Synthesis of Fluorobenzene and Benzimidazole Nucleic-Acid Analogues and Their Influence on Stability of RNA Duplexes

  摘要：

  Six different ribonucleoside phosphoramidites with fluorobenzenes or fluorobenzimidazoles as base analogues, one abasic site, and inosine were synthesized and incorporated into oligoribonucleotides. The oligomers were investigated by means of UV and CD spectroscopy to assess the contribution of H-bonding, base stacking, and solvation to the stability of the RNA duplex. CD Spectra show that the incorporation of modified nucleosides does not lead to changes in the structure of RNA. The T-m differences determined are based on changes in base stacking and solvation. Individual contributions of base stacking and solvation of the modified nucleosides could be determined. In fluorobenzene . fluorobenzimidazole-modified base pairs, a duplex-stabilizing force was found that points to a weak F ... H H-bond.

  DOI：

  10.1002/1522-2675(20000809)83:8<1791::aid-hlca1791>3.0.co;2-k