tert-butyl (4-(((3a'S,3b'R,9a'S,11'R,11a'S)-3a',3b',9a',10',11',11a'-hexahydro-5'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazin]-11'-yl)amino)-4-oxobutyl)carbamate | 1554421-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: tert-butyl (4-(((3a'S,3b'R,9a'S,11'R,11a'S)-3a',3b',9a',10',11',11a'-hexahydro-5'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazin]-11'-yl)amino)-4-oxobutyl)carbamate
• CAS: 1554421-75-8
• 化学式: C₂₄H₃₇N₅O₆
• 分子量: 491.588
• InChiKey: PMNADTICRAVEHU-KZEVZHLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  125.83
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-(((3a'S,3b'R,9a'S,11'R,11a'S)-3a',3b',9a',10',11',11a'-hexahydro-5'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazin]-11'-yl)amino)-4-oxobutyl)carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以79%的产率得到4-amino-N-((5aR,6R,7S,8R,9aS)-6,7-dihydroxy-5a,6, 7,8,9,9ahexahydro-4H-benzo[b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl)butanamide
  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：

  (3aS,3bR,9aS,11R,11aS)-11-azido-3b,5,9a,10,11,11a-hexahydro-3aH-spiro[[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-2,1'-cyclohexane] 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 三甲基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 tert-butyl (4-(((3a'S,3b'R,9a'S,11'R,11a'S)-3a',3b',9a',10',11',11a'-hexahydro-5'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4',5':5,6]benzo[1,2-b][1,2,3]triazolo[1,5-d][1,4]oxazin]-11'-yl)amino)-4-oxobutyl)carbamate
  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