(1S,2R,3S,4S)-5-Chloro-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-pentane-1,2,3,4-tetraol | 210108-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,2R,3S,4S)-5-Chloro-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-pentane-1,2,3,4-tetraol
• CAS: 210108-67-1
• 化学式: C₁₃H₁₆ClN₃O₄
• 分子量: 313.741
• InChiKey: KKTIWLUTUAEOLZ-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111.63
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S)-5-Chloro-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-pentane-1,2,3,4-tetraol 在 吡啶 、 对甲苯磺酸 作用下， 反应 24.0h， 生成 4-((4R,5S,4'S,5'S)-5'-Chloromethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-2-phenyl-2H-[1,2,3]triazole
  参考文献：
  名称：

  Homo-C-Nucleoside Analogs† II. Synthesis and Anomeric Configuration of 4-(2,5-Anhydro-D-Gluco-PEntitol-1-YL)-2-Phenyl2H-1,2,3-Triazole††

  摘要：

  Treatment of 4-(D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (1) with p-toluenesulfonyl chloride in pyridine solution, afforded the homo-C-nucleoside analog, 4-(2,5-anhydro-D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (2) as well as its partial p-toluenesulfonyl derivative (3). 4-(5-Chloro-5-deoxy-D-gluco-pentitol-1-yl)2-phenyl-2H-1,2,3-triazole (8), was isolated as a byproduct from the reaction. The structure and anomeric configuration of 2 was determined by acylation, H-1, C-13 NMR, and NOE, spectroscopy as well as mass spectrometry.

  DOI：

  10.1080/07328319808004234
• 作为产物：
  描述：

  (1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-D-arabitol 在 吡啶 、 对甲苯磺酰氯 作用下， 以3%的产率得到Toluene-4-sulfonic acid (3R,4S,5R)-4-hydroxy-5-[(R)-hydroxy-(2-phenyl-2H-[1,2,3]triazol-4-yl)-methyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Homo-C-Nucleoside Analogs† II. Synthesis and Anomeric Configuration of 4-(2,5-Anhydro-D-Gluco-PEntitol-1-YL)-2-Phenyl2H-1,2,3-Triazole††

  摘要：

  Treatment of 4-(D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (1) with p-toluenesulfonyl chloride in pyridine solution, afforded the homo-C-nucleoside analog, 4-(2,5-anhydro-D-gluco-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole (2) as well as its partial p-toluenesulfonyl derivative (3). 4-(5-Chloro-5-deoxy-D-gluco-pentitol-1-yl)2-phenyl-2H-1,2,3-triazole (8), was isolated as a byproduct from the reaction. The structure and anomeric configuration of 2 was determined by acylation, H-1, C-13 NMR, and NOE, spectroscopy as well as mass spectrometry.

  DOI：

  10.1080/07328319808004234