3'-O-(tert-butyldiphenylsilyl)-(5'S)-C-(1-azidopent-3-enyl)-thymidine | 1219002-42-2

• 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: 3'-O-(tert-butyldiphenylsilyl)-(5'S)-C-(1-azidopent-3-enyl)-thymidine
• CAS: 1219002-42-2
• 化学式: C₃₁H₃₉N₅O₅Si
• 分子量: 589.767
• InChiKey: CXQWASJIYHIHIB-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  142.31
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3'-O-(tert-butyldiphenylsilyl)-(5'S)-C-(1-azidopent-3-enyl)-thymidine 、 1-iodo-4-(prop-2-yn-1-yloxy)benzene 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 以89%的产率得到1-((2R,4S,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-((S)-1-hydroxy-6-(4-((4-iodophenoxy)methyl)-1H-1,2,3-triazol-1-yl)hex-3-en-1-yl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A ‘click chemistry’ approach to the efficient synthesis of modified nucleosides and oligonucleotides for PET imaging

  摘要：

  Different thymidine derivatives bearing either an iodoaryl moiety at the 5' position or a dialkylsilyl group at the 3' position have been efficiently synthesized as precursors for carbon-11 or fluorine-18 labeling, respectively. Furthermore, iodoarylated thymidine derivatives have been incorporated into oligonucleotides giving an original way to label them with carbon-11. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.120
• 作为产物：
  描述：

  3'-O-(tert-butyldiphenylsilyl)-(5'S)-C-(bromo-1-pent-3-ene)-thymidine 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以95%的产率得到3'-O-(tert-butyldiphenylsilyl)-(5'S)-C-(1-azidopent-3-enyl)-thymidine
  参考文献：
  名称：

  A ‘click chemistry’ approach to the efficient synthesis of modified nucleosides and oligonucleotides for PET imaging

  摘要：

  Different thymidine derivatives bearing either an iodoaryl moiety at the 5' position or a dialkylsilyl group at the 3' position have been efficiently synthesized as precursors for carbon-11 or fluorine-18 labeling, respectively. Furthermore, iodoarylated thymidine derivatives have been incorporated into oligonucleotides giving an original way to label them with carbon-11. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.12.120