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 | 175650-98-3

• 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: 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
• CAS: 175650-98-3
• 化学式: C₃₇H₄₅FN₂O₈Si
• 分子量: 692.857
• InChiKey: HGASXRWAHJLNKV-UKNNOAMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.07
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  110.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 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 在 四氮唑 作用下， 以 乙腈 为溶剂， 以71%的产率得到
  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 咪唑 、 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 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