1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione | 1173882-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1173882-43-3
• 化学式: C₂₄H₂₇N₇O₇
• 分子量: 525.521
• InChiKey: WLEBHLFLTFGJHC-VTYCOLDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione 、 1-[(2R,4S,5R)-4-azido-5-[[1-[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(3-trimethylsilylprop-2-ynyl)oxolan-3-yl]triazol-4-yl]methyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 二甲基硫 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 以95%的产率得到
  参考文献：
  名称：

  Convergent synthesis of oligomers of triazole-linked DNA analogue (TLDNA) in solution phase

  摘要：

  A convergent route for the solution-phase synthesis of oligomeric triazole-linked analogues of DNA ((TL)DNA) has been developed. A one-pot procedure for desilylation of masked acetylene and the ensuing copper-catalyzed Huisgen coupling reaction between oligomers allowed the solution-phase synthesis of 7-mer and 8-mer (TL)DNA in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.101
• 作为产物：
  描述：

  1-((2R,4S,5R)-4-hydroxy-5-((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-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以96.8 mg的产率得到1-[(2R,4S,5R)-4-[4-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-1-yl]-5-prop-2-ynyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Convergent synthesis of oligomers of triazole-linked DNA analogue (TLDNA) in solution phase

  摘要：

  A convergent route for the solution-phase synthesis of oligomeric triazole-linked analogues of DNA ((TL)DNA) has been developed. A one-pot procedure for desilylation of masked acetylene and the ensuing copper-catalyzed Huisgen coupling reaction between oligomers allowed the solution-phase synthesis of 7-mer and 8-mer (TL)DNA in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.101

文献信息

• Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA
  作者：Hiroyuki Isobe、Tomoko Fujino、Naomi Yamazaki、Marine Guillot-Nieckowski、Eiichi Nakamura

  DOI：10.1021/ol801230k

  日期：2008.9.1

  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.