1-(methyl 5-deoxy-α-D-arabinofuranosid-5-yl)-4-n-pentyl-1H-1,2,3-triazole | 1033538-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(methyl 5-deoxy-α-D-arabinofuranosid-5-yl)-4-n-pentyl-1H-1,2,3-triazole
• 英文别名: (2S,3S,4S,5R)-2-methoxy-5-[(4-pentyltriazol-1-yl)methyl]oxolane-3,4-diol
• CAS: 1033538-15-6
• 化学式: C₁₃H₂₃N₃O₄
• 分子量: 285.343
• InChiKey: SFWKRNRNAONTQE-NDBYEHHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 5-azido-5-deoxy-α-D-arabinofuranoside 、 1-庚炔 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 14.0h， 以60%的产率得到1-(methyl 5-deoxy-α-D-arabinofuranosid-5-yl)-4-n-pentyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents

  摘要：

  5-Azido-5-deoxy-xylo-, ribo-, and arabinofuranoses were prepared by the reaction of the respective 5-O-(methanesulfonyl) or p-toluenesulfonyl derivatives with NaN3 in DMF. The intermediate 5-azido-5-deoxy glycofuranoses on 1,3-cycloaddition with different alkynes in the presence Of CUSO4 and sodium ascorbate gave the corresponding sugar triazoles in very good yields. The synthesized sugar triazoles were evaluated for their antitubercular activity against Mycobacterium tuberculosis H37Rv, where one of the compounds displayed mild antitubercular activity in vitro with MIC 12.5 mu g/mL. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.013

文献信息

• Preparation and reactions of sugar azides with alkynes: synthesis of sugar triazoles as antitubercular agents
  作者：Biswajit Kumar Singh、Amit Kumar Yadav、Brijesh Kumar、A. Gaikwad、Sudhir Kumar Sinha、Vinita Chaturvedi、Rama Pati Tripathi

  DOI：10.1016/j.carres.2008.02.013

  日期：2008.5

  5-Azido-5-deoxy-xylo-, ribo-, and arabinofuranoses were prepared by the reaction of the respective 5-O-(methanesulfonyl) or p-toluenesulfonyl derivatives with NaN3 in DMF. The intermediate 5-azido-5-deoxy glycofuranoses on 1,3-cycloaddition with different alkynes in the presence Of CUSO4 and sodium ascorbate gave the corresponding sugar triazoles in very good yields. The synthesized sugar triazoles were evaluated for their antitubercular activity against Mycobacterium tuberculosis H37Rv, where one of the compounds displayed mild antitubercular activity in vitro with MIC 12.5 mu g/mL. (c) 2008 Elsevier Ltd. All rights reserved.