3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(3-iodophenyl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile | 909869-67-6

• 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: 3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(3-iodophenyl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 909869-67-6
• 化学式: C₄₁H₄₈IN₂O₆P
• 分子量: 822.72
• InChiKey: WKYBXNPPKJGNDH-XDYREYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-O-(4,4'-dimethoxytrityl)-1,2-deoxy-β-1-(3-iodophenyl)-D-ribofuranose 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到3-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(3-iodophenyl)oxolan-3-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
  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