(3aR,5S,6R,7S,7aS)-5-azido-6-(2-oxo-2-(piperidin-1-yl)eth-oxy)-7-(prop-2-yn-1-yloxy)hexahydrobenzo[d]oxazol-2(3H)-one | 1554421-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aR,5S,6R,7S,7aS)-5-azido-6-(2-oxo-2-(piperidin-1-yl)eth-oxy)-7-(prop-2-yn-1-yloxy)hexahydrobenzo[d]oxazol-2(3H)-one
• CAS: 1554421-86-1
• 化学式: C₁₇H₂₃N₅O₅
• 分子量: 377.4
• InChiKey: PPFHDTOEDGUZJL-CQOGHXNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  125.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6R,7S,7aS)-5-azido-6-(2-oxo-2-(piperidin-1-yl)eth-oxy)-7-(prop-2-yn-1-yloxy)hexahydrobenzo[d]oxazol-2(3H)-one 在 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 (3aR,5S,6R,7S,7aS)-5-amino-6-(2-oxo-2-(piperidin-1-yl)ethoxy)-7-(prop-2-yn-1-yloxy)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
• 作为产物：
  描述：

  (3aR,5S,6R,7S,7aS)-5-azido-7-hydroxy-3-(4-methoxybenzyl)-6-(methoxymethoxy)hexahydrobenzo[d]oxazol-2(3H)-one 在 盐酸 、 ammonium cerium (IV) nitrate 、 sodium hexamethyldisilazane 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 32.08h， 生成 (3aR,5S,6R,7S,7aS)-5-azido-6-(2-oxo-2-(piperidin-1-yl)eth-oxy)-7-(prop-2-yn-1-yloxy)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