(1S,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anecarbonitrile | 1223053-83-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1S,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anecarbonitrile
• 英文别名: (1S,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohexane-1-carbonitrile
• CAS: 1223053-83-5
• 化学式: C₉H₁₃N₇O₂
• 分子量: 251.248
• InChiKey: SKKTTXCLQAXHIS-HXFLIBJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anecarbonitrile 在 三苯基膦 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of 2,4,5-triaminocyclohexanecarboxylic acid as a novel 2-deoxystreptamine mimic

  摘要：

  Since aminoglycosides have been known to exert their antibacterial activities by binding to various RNA targets, 2-deoxystreptamine served as a particularly important model in understanding RNA-small molecule interaction. Herein, 2,4,5-triaminocyclohexanecarboxylic acid was prepared as a novel 2-deoxystreptamine (2-DOS) mimic, which replaces highly flexible glycosidic bonds of aminoglycosides with amide bonds and may improve binding selectivity toward RNA targets through increased rigidity and additional hydrogen-bonding capability. This unnatural g-amino acid can also be used as a potential component for synthetic foldamers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.111
• 作为产物：
  描述：

  sodium cyanide 、 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (1S,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anecarbonitrile
  参考文献：
  名称：

  Synthesis of 2,4,5-triaminocyclohexanecarboxylic acid as a novel 2-deoxystreptamine mimic

  摘要：

  Since aminoglycosides have been known to exert their antibacterial activities by binding to various RNA targets, 2-deoxystreptamine served as a particularly important model in understanding RNA-small molecule interaction. Herein, 2,4,5-triaminocyclohexanecarboxylic acid was prepared as a novel 2-deoxystreptamine (2-DOS) mimic, which replaces highly flexible glycosidic bonds of aminoglycosides with amide bonds and may improve binding selectivity toward RNA targets through increased rigidity and additional hydrogen-bonding capability. This unnatural g-amino acid can also be used as a potential component for synthetic foldamers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.111

文献信息

• Synthesis of 2,4,5-triaminocyclohexanecarboxylic acid as a novel 2-deoxystreptamine mimic
  作者：Sarah Roberts、Maruthi Chittapragada、Krishnaiah Pendem、Brandon J. Leavitt、John W. Mahler、Young Wan Ham

  DOI：10.1016/j.tetlet.2010.01.111

  日期：2010.3

  Since aminoglycosides have been known to exert their antibacterial activities by binding to various RNA targets, 2-deoxystreptamine served as a particularly important model in understanding RNA-small molecule interaction. Herein, 2,4,5-triaminocyclohexanecarboxylic acid was prepared as a novel 2-deoxystreptamine (2-DOS) mimic, which replaces highly flexible glycosidic bonds of aminoglycosides with amide bonds and may improve binding selectivity toward RNA targets through increased rigidity and additional hydrogen-bonding capability. This unnatural g-amino acid can also be used as a potential component for synthetic foldamers. (C) 2010 Elsevier Ltd. All rights reserved.