[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate | 1038443-06-9

• 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: [(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1038443-06-9
• 化学式: C₅₆H₆₅N₁₇O₁₉S
• 分子量: 1312.3
• InChiKey: FMLMKJCJISMPSD-VHNPIMQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  93
• 可旋转键数：
  23
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  426
• 氢给体数：
  5
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以93%的产率得到1-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[4-[[(2R,3S,5R)-2-[[4-[[(2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  铜（I）催化的[3 + 2]环加成反应快速高效地微波辅助合成3'，5'-戊啶

  摘要：

  从5'- O-甲苯磺酰基胸苷开始，顺序叠氮化和Cu催化的[3 + 2]叠氮化物-炔烃1,3-偶极环加成反应导致高产量地形成3'，5'-戊啶。整个过程仅需要后处理/沉淀步骤，由于微波活化，仅需18分钟即可完成。

  DOI：

  10.1016/j.tet.2008.04.006
• 作为产物：
  描述：

  3'-O-propargyl-5'-O-tosylthymidine 、 1-[(2R,4S,5R)-5-[[4-[[(2R,3S,5R)-2-[[4-[[(2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxymethyl]triazol-1-yl]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.05h， 以72%的产率得到[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-[[1-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]triazol-4-yl]methoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  铜（I）催化的[3 + 2]环加成反应快速高效地微波辅助合成3'，5'-戊啶

  摘要：

  从5'- O-甲苯磺酰基胸苷开始，顺序叠氮化和Cu催化的[3 + 2]叠氮化物-炔烃1,3-偶极环加成反应导致高产量地形成3'，5'-戊啶。整个过程仅需要后处理/沉淀步骤，由于微波活化，仅需18分钟即可完成。

  DOI：

  10.1016/j.tet.2008.04.006

文献信息

• A rapid efficient microwave-assisted synthesis of a 3′,5′-pentathymidine by copper(I)-catalyzed [3+2] cycloaddition
  作者：Romain Lucas、Rachida Zerrouki、Robert Granet、Pierre Krausz、Yves Champavier

  DOI：10.1016/j.tet.2008.04.006

  日期：2008.6

  Starting from 5′-O-tosylthymidine, sequential azidation and Cu-catalyzed [3+2] azide–alkyne 1,3-dipolar cycloaddition led to the formation of a 3′,5′-pentathymidine in high yield. The whole process needed only work-up/precipitation steps and was completed within just 18 min, thanks to microwave activation.

  从5'- O-甲苯磺酰基胸苷开始，顺序叠氮化和Cu催化的[3 + 2]叠氮化物-炔烃1,3-偶极环加成反应导致高产量地形成3'，5'-戊啶。整个过程仅需要后处理/沉淀步骤，由于微波活化，仅需18分钟即可完成。