1,2-dideoxy-β-1-(2,4-difluoro-3-iodophenyl)-D-ribofuranose | 1005741-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dideoxy-β-1-(2,4-difluoro-3-iodophenyl)-D-ribofuranose
• 英文别名: (2R,3S,5R)-5-(2,4-difluoro-3-iodophenyl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1005741-43-4
• 化学式: C₁₁H₁₁F₂IO₃
• 分子量: 356.108
• InChiKey: XOMUGEIOJPDZEJ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1,2-dideoxy-α-1-(2,4-difluoro-3-iodophenyl)-D-ribofuranose 、 1,2-dideoxy-β-1-(2,4-difluoro-3-iodophenyl)-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs

  摘要：

  [GRAPHICS]Ab initio calculations of halogen bond energies of artificial base pairs constructed between iodinated aromatic nucleobase mimics and nitrogen-containing acceptor molecules such as pyridine and imidazole suggest that modified base pairs are converted to optimized planar base pairs with weak Delta E values of -0.19 to -3.93 kcal/mol. To evaluate the contribution of halogen bonding toward duplex stabilization of such modified nucleobase mimics introduced into artificial base pairs, we synthesized three C-nucleoside analogues 1-3 with several iodinated aromatic rings and an imidazole nucleoside derivative 4 and incorporated them into oligodeoxynucleotides. Hybridization studies of modified oligodeoxynucleotides incorporating iodoaromatic bases showed their unique universal base-like ability; however, no indication of halogen bond formation was observed. A more sophisticated design is required for the development of new base pairs stabilized by halogen bonding.

  DOI：

  10.1021/jo701634t