5'-O-dimethoxytrityl-4-O-methyl-5-fluorouridine | 175650-97-2

• 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: 5'-O-dimethoxytrityl-4-O-methyl-5-fluorouridine
• CAS: 175650-97-2
• 化学式: C₃₁H₃₁FN₂O₈
• 分子量: 578.594
• InChiKey: XVKSJQLBOVUFIK-LTGLEFCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  121.5
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-O-dimethoxytrityl-4-O-methyl-5-fluorouridine 在 咪唑 、 四氮唑 作用下， 以 吡啶 、 乙腈 为溶剂， 生成
  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 吡啶 、 甲醇 为溶剂， 反应 128.25h， 生成 5'-O-dimethoxytrityl-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

文献信息

• 5-Fluoro-4-thiouridine phosphoramidite: New synthon for introducing photoaffinity label into oligodeoxynucleotides
  作者：Jan Milecki、Joanna Nowak、Bohdan Skalski、Stefan Franzen

  DOI：10.1016/j.bmc.2011.08.035

  日期：2011.10

  appropriate set of protecting groups was optimized including the 4-thio function introduced via 4-triazolyl as the 4-(2-cyanoethyl)thio derivative, and the t-butyldimethyl silyl for 2′ and 3′ hydroxyl protection, enabling efficient synthesis of the phosphoramidite. These protecting groups prevented unwanted side reactions during oligonucleotide synthesis. The utility of the proposed synthetic route was proven

  描述了5-氟-4-硫代2'- O-甲基尿苷的亚磷酰胺的合成。优化了一组合适的保护基团，包括通过4-三唑基作为4-（2-氰基乙基）硫代衍生物引入的4-硫基官能团，以及用于2'和3'羟基保护的叔丁基二甲基甲硅烷基，从而能够有效地合成亚磷酰胺。这些保护基团防止了寡核苷酸合成过程中的有害副反应。通过自动合成制备几种寡核苷酸，证明了所提出的合成路线的实用性。光化学实验证实了合成子的实用性。