1-[(2R,4S,5S)-4-azido-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2-one | 170236-32-5

• 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,4S,5S)-4-azido-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
• CAS: 170236-32-5
• 化学式: C₃₃H₃₂N₈O₅
• 分子量: 620.668
• InChiKey: UNYZATFTWKIPII-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5S)-4-azido-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2-one 在 吡啶 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-N4-benzoyl-2',3'-dideoxy-3'-azido-5-methylcytidine
  参考文献：
  名称：

  Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures

  摘要：

  Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.

  DOI：

  10.1021/ol070990u
• 作为产物：
  描述：

  齐多夫定 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 8.5h， 生成 1-[(2R,4S,5S)-4-azido-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-2-yl]-5-methyl-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and RNA Binding Selectivity of Oligonucleotides Modified with Five-Atom Thioacetamido Nucleic Acid Backbone Structures

  摘要：

  Convenient chemical synthesis and incorporation of dithymidine and thymidine-cytidine dimer blocks connected with a five-atom amide linker N3'-CO-CH2-S-CH2 into oligonucleotides (ONs) are reported. The UV-T-m experiments for binding affinities of these mixed backbone ONs with complementary DNA and RNA sequences revealed important results such as significantly higher RNA-binding selectivity as compared with complementary DNA. NMR studies of the dimer blocks suggested a marginal increase in the N-type sugar conformations over that of the native DNA.

  DOI：

  10.1021/ol070990u