| 1190883-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1190883-36-3
• 化学式: C₁₃H₁₅BrO₅S
• 分子量: 363.229
• InChiKey: JWCJQYBXKMZRRZ-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 以98%的产率得到1β-(5-bromothiophen-2-yl)-1,2-dideoxy-D-ribofuranose
  参考文献：
  名称：

  Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases

  摘要：

  The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.021
• 作为产物：
  描述：

  (2R,3S)-5-(5-bromothiophen-2-yl)-2-(hydroxymethyl)oxolan-3-ol 、 乙酸酐 在 吡啶 作用下， 生成 、
  参考文献：
  名称：

  Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases

  摘要：

  The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.021