5'-O-(t-butyldimethylsilyl)-3'-deoxy-3'-(5-deutero-4-(p-tolyl)-1H-1,2,3-triazol-1-yl)thymidine | 1401307-43-4

• 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: 5'-O-(t-butyldimethylsilyl)-3'-deoxy-3'-(5-deutero-4-(p-tolyl)-1H-1,2,3-triazol-1-yl)thymidine
• 英文别名: 1-[(2R,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[5-deuterio-4-(4-methylphenyl)triazol-1-yl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1401307-43-4
• 化学式: C₂₅H₃₅N₅O₄Si
• 分子量: 498.662
• InChiKey: OGVJNNDOMIPRIV-UPGQPWJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  98.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3'-azido-3'-deoxy-5'-O-(t-butyldimethylsilyl)-thymidine 、 4-甲苯基乙炔 在 copper(ll) sulfate pentahydrate 、 重水 、 sodium ascorbate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以96%的产率得到5'-O-(t-butyldimethylsilyl)-3'-deoxy-3'-(5-deutero-4-(p-tolyl)-1H-1,2,3-triazol-1-yl)thymidine
  参考文献：
  名称：

  Synthesis of Deuterated 1,2,3-Triazoles

  摘要：

  The copper-catalyzed azide alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D+ ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

  DOI：

  10.1021/jo301146j