4-O-methyl-5-fluorouridine | 175651-05-5

• 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: 4-O-methyl-5-fluorouridine
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-4-methoxypyrimidin-2-one
• CAS: 175651-05-5
• 化学式: C₁₀H₁₃FN₂O₆
• 分子量: 276.221
• InChiKey: QCWNERCOUADAAT-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-methyl-5-fluorouridine 在 咪唑 作用下， 以 吡啶 为溶剂， 生成 1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-5-fluoro-4-methoxy-1H-pyrimidin-2-one
  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：

  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 、 三乙胺 、 4-氯苯基二氯磷酸酯 作用下， 以 甲醇 为溶剂， 反应 128.25h， 生成 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