2,3,5-tri-O-benzyl-1-deoxy-1-(3-fluorophenyl)-β-D-ribofuranose | 304436-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-1-deoxy-1-(3-fluorophenyl)-β-D-ribofuranose
• CAS: 304436-62-2
• 化学式: C₃₂H₃₁FO₄
• 分子量: 498.594
• InChiKey: LZTPXFKONSXECX-IQLXHWPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-1-deoxy-1-(3-fluorophenyl)-β-D-ribofuranose 在 palladium dihydroxide 三乙胺 、 环己烯 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 7.0h， 生成 1-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(3-fluorophenyl)-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
• 作为产物：
  描述：

  2,3,5-三苄氧基-D-核糖酸-1,4-内酯 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,3,5-tri-O-benzyl-1-deoxy-1-(3-fluorophenyl)-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