3,5-O-[1,1,3,3-tetraisopropyldisiloxanediyl]-1,2-dideoxy-1-β-(3-iodophenyl)-D-ribofuranose | 1005741-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-O-[1,1,3,3-tetraisopropyldisiloxanediyl]-1,2-dideoxy-1-β-(3-iodophenyl)-D-ribofuranose
• 英文别名: (6aR,8R,9aS)-8-(3-iodophenyl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocine
• CAS: 1005741-45-6
• 化学式: C₂₃H₃₉IO₄Si₂
• 分子量: 562.636
• InChiKey: UXVFUZIKZQCZPA-XPWALMASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (6aR,9aS)-8-(3-iodophenyl)-2,2,4,4-tetra(propan-2-yl)-6,6a,9,9a-tetrahydrofuro[3,2-f][1,3,5,2,4]trioxadisilocin-8-ol 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,5-O-[1,1,3,3-tetraisopropyldisiloxanediyl]-1,2-dideoxy-1-β-(3-iodophenyl)-D-ribofuranose 、 3,5-O-[1,1,3,3-tetraisopropyldisiloxanediyl]-1,2-dideoxy-1-α-(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