2',3',5'-tri-O-acetyl-4-O-methyl-5-fluorouridine | 175651-04-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3',5'-tri-O-acetyl-4-O-methyl-5-fluorouridine
• CAS: 175651-04-4
• 化学式: C₁₆H₁₉FN₂O₉
• 分子量: 402.333
• InChiKey: GXDCENKOOXZLDY-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  132.25
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-acetyl-4-O-methyl-5-fluorouridine 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以78%的产率得到4-O-methyl-5-fluorouridine
  参考文献：
  名称：

  ¹⁹F NMR of RNA. The Structural and Chemical Aspects of 5-Fluoro-cytidine and-uridine Labelling of Oligoribonucleotides

  摘要：

  Results of PM3 semiempirical calculation revealed that energy and hydrogen bonds geometry of 1-methyl-5-fluoro-uracil and -cytosine base-pairs with 9-methyladenine and -guanine respectively are virtually the same as for the natural bases. Analysis of proton coupling constants proved that the sugar puckering of 5-fluorouridine and 5-fluorocytidine is analogous to non-modified ribonucleosides. 5-Fluorocytidine was regioselectively introduced to oligoribonucleotides, prepared using 2'-O-tert-dimethylsilyl protection, via post-synthetic quantitative ammonolysis of 4-O-methyl-5-fluorouridine derived precursor.

  DOI：

  10.1080/07328319608002399
• 作为产物：
  描述：

  甲醇 、 2',3',5'-tri-O-acetyl-5-fluorouridine 在 1H-1,2,4-三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4-氯苯基二氯磷酸酯 作用下， 生成 2',3',5'-tri-O-acetyl-4-O-methyl-5-fluorouridine
  参考文献：
  名称：

  ¹⁹F NMR of RNA. The Structural and Chemical Aspects of 5-Fluoro-cytidine and-uridine Labelling of Oligoribonucleotides

  摘要：

  Results of PM3 semiempirical calculation revealed that energy and hydrogen bonds geometry of 1-methyl-5-fluoro-uracil and -cytosine base-pairs with 9-methyladenine and -guanine respectively are virtually the same as for the natural bases. Analysis of proton coupling constants proved that the sugar puckering of 5-fluorouridine and 5-fluorocytidine is analogous to non-modified ribonucleosides. 5-Fluorocytidine was regioselectively introduced to oligoribonucleotides, prepared using 2'-O-tert-dimethylsilyl protection, via post-synthetic quantitative ammonolysis of 4-O-methyl-5-fluorouridine derived precursor.

  DOI：

  10.1080/07328319608002399