4'-C-azidomethyl-3',5'-di-O-benzyl-2-O-methanesulfonyluridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-C-azidomethyl-3',5'-di-O-benzyl-2-O-methanesulfonyluridine
• 英文别名: [(2R,3R,4S,5R)-5-(azidomethyl)-2-(2,4-dioxopyrimidin-1-yl)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] methanesulfonate
• 化学式: C₂₅H₂₇N₅O₈S
• 分子量: 557.584
• InChiKey: AQVPYDXIHATCFK-STAYPELNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4'-C-azidomethyl-3',5'-di-O-benzyl-2-O-methanesulfonyluridine 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以91%的产率得到4′-C-azidomethyl-3′,5′-di-O-benzylarabinouridine
  参考文献：
  名称：

  Influence of 2′-Fluoro versus 2′-O-Methyl Substituent on the Sugar Puckering of 4′-C-Aminomethyluridine

  摘要：

  Herein, we report the synthesis of 4'-C-aminomethyl-2'-deoxy-2'-fluorouridine, a therapeutically appealing RNA modification. Conformational analysis by DFT calculations and molecular dynamics simulations using trinucleotide model systems revealed that modified sugar adopts C3'-endo conformation. In this conformer, a weak intramolecular C-H center dot center dot center dot F H-bond between the hydrogen atom of the 4'-C-CH2 group and the F atom at the 2' position is observed. Comparative studies with, unmodified, 2'-fluoro-, 2'-O-methyl-, and 4'-C-aminomethyl-2'-O-methyluridine showed the chemical nature of 2'-substituent dictates the sugar puckering of 2',4' modified nucleotides.

  DOI：

  10.1021/jo4012333
• 作为产物：
  描述：

  3',5'-di-O-benzyl-4'-C-azidomethyl-2'-O-acetyluridine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 4'-C-azidomethyl-3',5'-di-O-benzyl-2-O-methanesulfonyluridine
  参考文献：
  名称：

  Influence of 2′-Fluoro versus 2′-O-Methyl Substituent on the Sugar Puckering of 4′-C-Aminomethyluridine

  摘要：

  Herein, we report the synthesis of 4'-C-aminomethyl-2'-deoxy-2'-fluorouridine, a therapeutically appealing RNA modification. Conformational analysis by DFT calculations and molecular dynamics simulations using trinucleotide model systems revealed that modified sugar adopts C3'-endo conformation. In this conformer, a weak intramolecular C-H center dot center dot center dot F H-bond between the hydrogen atom of the 4'-C-CH2 group and the F atom at the 2' position is observed. Comparative studies with, unmodified, 2'-fluoro-, 2'-O-methyl-, and 4'-C-aminomethyl-2'-O-methyluridine showed the chemical nature of 2'-substituent dictates the sugar puckering of 2',4' modified nucleotides.

  DOI：

  10.1021/jo4012333

文献信息

• Influence of 2′-Fluoro versus 2′-<i>O</i>-Methyl Substituent on the Sugar Puckering of 4′-<i>C</i>-Aminomethyluridine
  作者：Kiran R. Gore、S. Harikrishna、P. I. Pradeepkumar

  DOI：10.1021/jo4012333

  日期：2013.10.4

  Herein, we report the synthesis of 4'-C-aminomethyl-2'-deoxy-2'-fluorouridine, a therapeutically appealing RNA modification. Conformational analysis by DFT calculations and molecular dynamics simulations using trinucleotide model systems revealed that modified sugar adopts C3'-endo conformation. In this conformer, a weak intramolecular C-H center dot center dot center dot F H-bond between the hydrogen atom of the 4'-C-CH2 group and the F atom at the 2' position is observed. Comparative studies with, unmodified, 2'-fluoro-, 2'-O-methyl-, and 4'-C-aminomethyl-2'-O-methyluridine showed the chemical nature of 2'-substituent dictates the sugar puckering of 2',4' modified nucleotides.