(1S,2R,4S,5S)-methyl-2,4-diazido-5-hydroxycyclohexane-carboxylate | 1223053-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,4S,5S)-methyl-2,4-diazido-5-hydroxycyclohexane-carboxylate
• 英文别名: methyl (1S,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexane-1-carboxylate
• CAS: 1223053-85-7
• 化学式: C₈H₁₂N₆O₃
• 分子量: 240.222
• InChiKey: MOYQDFASMLBBJV-VZFHVOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (1S,2R,4S,5S)-methyl-2,4-diazido-5-hydroxycyclohexane-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 反应 12.0h， 以92%的产率得到(1S,2R,4S,5S)-methyl-2,4-bis(t-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate
  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：

  甲醇 、 (1S,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexane-1-carbonitrile 在 盐酸 作用下， 生成 (1S,2R,4S,5S)-methyl-2,4-diazido-5-hydroxycyclohexane-carboxylate
  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