N-(2-azidoethyl)-N,N-bis{4-[1-(2-deoxy-β-D-ribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine | 1420296-04-3

• 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: N-(2-azidoethyl)-N,N-bis{4-[1-(2-deoxy-β-D-ribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine
• CAS: 1420296-04-3
• 化学式: C₃₂H₄₄N₁₄O₁₀
• 分子量: 784.789
• InChiKey: JAGHRNHXJMISOV-BQXGFVACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.18
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  300.8
• 氢给体数：
  4.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  N-(2-azidoethyl)-N,N-bis{4-[1-(2-deoxy-β-D-ribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine 、 5-(dimethylamino)-N-(prop-2-yn-1-yl)naphthalene-1-sulfonamide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以73%的产率得到N-[(4-dansylaminomethyl)-1,2,3-triazol-1-ylethyl]-N,N-bis{4-[1-(2-deoxy-β-D-ribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine
  参考文献：
  名称：

  Tris(azidoethyl)amine Hydrochloride; a Versatile Reagent for Synthesis of Functionalized Dumbbell Oligodeoxynucleotides

  摘要：

  Triazole-cross-linked oligodeoxynucleotides were synthesized using the Cu(I) catalyzed allryne-azide cycloaddition with tris(azidoethyl)amine hydrochloride and oligodeoxynucleotides possessing N-3-(propargyl)thymidine at both the 3'- and 5'-terminl. Further installation of a functional molecule to the dumbbell oligodeoxynucleotides was achieved by utilizing the remaining azide group.

  DOI：

  10.1021/ol400001w
• 作为产物：
  描述：

  N-(2-azidoethyl)-N,N-bis{4-[1-(2-deoxy-5-O-4′,4′′-dimethoxytrityl-β-dribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以58%的产率得到N-(2-azidoethyl)-N,N-bis{4-[1-(2-deoxy-β-D-ribofuranosyl)thymin-3-ylmethyl]-1,2,3-triazol-1-ylethyl}amine
  参考文献：
  名称：

  Tris(azidoethyl)amine Hydrochloride; a Versatile Reagent for Synthesis of Functionalized Dumbbell Oligodeoxynucleotides

  摘要：

  Triazole-cross-linked oligodeoxynucleotides were synthesized using the Cu(I) catalyzed allryne-azide cycloaddition with tris(azidoethyl)amine hydrochloride and oligodeoxynucleotides possessing N-3-(propargyl)thymidine at both the 3'- and 5'-terminl. Further installation of a functional molecule to the dumbbell oligodeoxynucleotides was achieved by utilizing the remaining azide group.

  DOI：

  10.1021/ol400001w