3'-O-benzoyl-2',5'-dideoxy-5'-ethynylthymidine | 945971-36-8

• 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: 3'-O-benzoyl-2',5'-dideoxy-5'-ethynylthymidine
• 英文别名: [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-prop-2-ynyloxolan-3-yl] benzoate
• CAS: 945971-36-8
• 化学式: C₁₉H₁₈N₂O₅
• 分子量: 354.362
• InChiKey: AJRWOKQVFBNPQJ-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynylthymidine 、 3'-O-benzoyl-2',5'-dideoxy-5'-ethynylthymidine 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以82%的产率得到(2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((1-((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-(3-(trimethylsilyl)prop-2-yn-1-yl)tetrahydrofuran-3-yl)-1H-1,2,3-triazol-4-yl)methyl)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

  摘要：

  A new triazole-linked analogue of DNA ((TL)DNA) has been designed and synthesized using click chemistry. The chain elongation reaction using copper-catalyzed Huisgen cycloaddition was successful and gave the artificial oligonucleotide that formed a stable double strand with the complementary strand of natural DNA.

  DOI：

  10.1021/ol801230k
• 作为产物：
  描述：

  苯甲酸 、 2',5'-dideoxy-5'-ethynyl-3'-epi-thymidine 在 偶氮二甲酸二异丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到3'-O-benzoyl-2',5'-dideoxy-5'-ethynylthymidine
  参考文献：
  名称：

  Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

  摘要：

  A new triazole-linked analogue of DNA ((TL)DNA) has been designed and synthesized using click chemistry. The chain elongation reaction using copper-catalyzed Huisgen cycloaddition was successful and gave the artificial oligonucleotide that formed a stable double strand with the complementary strand of natural DNA.

  DOI：

  10.1021/ol801230k