(1R,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anol | 1223053-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anol
• 英文别名: (1R,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohexan-1-ol
• CAS: 1223053-81-3
• 化学式: C₈H₁₄N₆O₃
• 分子量: 242.238
• InChiKey: SWNQCVKEWNYLOE-CWKFCGSDSA-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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anol 在 盐酸 、 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 palladium on carbon 、 水 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.83h， 生成 di-tert-butyl ((1R,3S,4S,6R)-4-amino-6-methoxycyclohexane-1,3-diyl)dicarbamate
  参考文献：
  名称：

  Conjugate of neamine and 2-deoxystreptamine mimic connected by an amide bond

  摘要：

  An amino-functionalized 2-deoxystreptamine (2-DOS) mimic was conjugated by an amide bond to a neamine moiety containing a carboxylic acid in ring II. A library of A-site RNA and its mutants was prepared to examine RNA binding characteristics of the additional 2-DOS moiety attached to neamine. The 2-DOS mimic conjugated to the neamine increased binding affinity up to 200-folds compared to that of neamine. The conjugate binds to native A-site RNA and its mutants with up to 6-fold difference in sequence selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.084
• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以92%的产率得到(1R,2R,4S,5S)-2,4-diazido-5-(methoxymethoxy)cyclohex-anol
  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