D-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol | 205990-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: D-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol
• 英文别名: D-(1S)-1-(2-Phenyl-2H-[1,2,3]triazol-4-yl)-erythrit；(1S,2S,3R)-1-(2-phenyltriazol-4-yl)butane-1,2,3,4-tetrol
• CAS: 205990-41-6
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: JNMUJXXKLZFAIT-GRYCIOLGSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  595.6±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 在 吡啶 、 三氟甲烷磺酰氯 作用下， 反应 24.0h， 以36%的产率得到β-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Studies ON Epimeric-D-asabino-and-D-ribo-tetritol-1-yl-2-phenyl-2 H-1,2,3-triazoles. Synthesis and Anomeric Configuration of 4-(α-and β-D-Erythrofuranosyl)-2-phenyl-2 H-1,2,3-Triazole C-Nucleoside Analogs

  摘要：

  Treatment of 4-(D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analogs, 4-(alpha-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (2) in 25% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(3). Treatment of the epimeric 4-(D-ribo-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(8) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analogs, 4-(beta-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (9) in 23% yield. Similar treatment of 8 with trifluoromethanesulfonyl chloride in pyridine solution afforded 9. The structure and anomeric configuration of these compounds were determined by acylation, NMR, NOE, circular dichroism spectroscopy and mass spectrometry.

  DOI：

  10.1080/07328319808004674
• 作为产物：
  描述：

  D-allose osazone 在 水 、 copper(II) sulfate 作用下， 生成 D-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol
  参考文献：
  名称：

  The Action of Copper Sulfate on the Phenyl Osazones of the Sugars. II. Some New Osotriazoles

  摘要：

  DOI：

  10.1021/ja01222a018

文献信息

• The Action of Copper Sulfate on the Phenyl Osazones of the Sugars. II. Some New Osotriazoles
  作者：W. T. Haskins、Raymond M. Hann、C. S. Hudson

  DOI：10.1021/ja01222a018

  日期：1945.6
• Studies ON Epimeric-D-<i>asabino</i>-and-D-<i>ribo</i>-tetritol-1-yl-2-phenyl-2 <i>H</i>-1,2,3-triazoles. Synthesis and Anomeric Configuration of 4-(α-and β-D-Erythrofuranosyl)-2-phenyl-2 <i>H</i>-1,2,3-Triazole <i>C</i>-Nucleoside Analogs
  作者：Mohammed A.E. Sallam、Farida F. Louis、John M. Cassady

  DOI：10.1080/07328319808004674

  日期：1998.4

  Treatment of 4-(D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analogs, 4-(alpha-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (2) in 25% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-arabino-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(3). Treatment of the epimeric 4-(D-ribo-tetritol-1-yl)-2-phenyl-2 H-1,2,3-triazole(8) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analogs, 4-(beta-D-erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (9) in 23% yield. Similar treatment of 8 with trifluoromethanesulfonyl chloride in pyridine solution afforded 9. The structure and anomeric configuration of these compounds were determined by acylation, NMR, NOE, circular dichroism spectroscopy and mass spectrometry.