(3aR,5S,6R,7S,7aS)-6,7-dihydroxy-5-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)hexahydrobenzo[d]oxazol-2(3H)-one | 1554421-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,5S,6R,7S,7aS)-6,7-dihydroxy-5-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)hexahydrobenzo[d]oxazol-2(3H)-one
• CAS: 1554421-48-5
• 化学式: C₁₀H₁₄N₄O₅
• 分子量: 270.245
• InChiKey: SKCOGUMYOZZJGV-DMAGGPPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.09
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  129.73
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6R,7S,7aS)-6,7-dihydroxy-5-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)hexahydrobenzo[d]oxazol-2(3H)-one 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以77%的产率得到(1R,2R,3S,4R,6S)-4-amino-6-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)cyclohex-ane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of triazole-functionalized 2-DOS analogues and their evaluation as A-site binders

  摘要：

  Aminoglycoside-antibiotics represent important tools for studying the biological functions of RNA. An orthogonal protection strategy applied on 2-deoxystreptamine (2-DOS) revealed a series of key intermediates that enable its regioselective functionalization. Our approach allowed the construction of selected representatives of triazole-containing analogues with diverse molecular frameworks for biological evaluation regarding their binding and antibacterial potencies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.125
• 作为产物：
  描述：

  (3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one 在 盐酸 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (3aR,5S,6R,7S,7aS)-6,7-dihydroxy-5-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)hexahydrobenzo[d]oxazol-2(3H)-one
  参考文献：
  名称：

  Synthesis of triazole-functionalized 2-DOS analogues and their evaluation as A-site binders

  摘要：

  Aminoglycoside-antibiotics represent important tools for studying the biological functions of RNA. An orthogonal protection strategy applied on 2-deoxystreptamine (2-DOS) revealed a series of key intermediates that enable its regioselective functionalization. Our approach allowed the construction of selected representatives of triazole-containing analogues with diverse molecular frameworks for biological evaluation regarding their binding and antibacterial potencies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.125