(1R,2R,4S,5S)-2,4-diazido-N-((1S,2S,4R,5R)-2,4-diamino-5-methoxycyclohexyl)-5-hydroxycyclohexanecarboxamide | 1331825-40-1

• 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-N-((1S,2S,4R,5R)-2,4-diamino-5-methoxycyclohexyl)-5-hydroxycyclohexanecarboxamide
• CAS: 1331825-40-1
• 化学式: C₁₄H₂₁N₁₃O₃
• 分子量: 419.406
• InChiKey: QYJKALSEZLHZQV-HMLLYTSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  253.6
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2,6-diazido-2,6-dideoxy-1-thio-β-D-glucopyranoside 、 (1R,2R,4S,5S)-2,4-diazido-N-((1S,2S,4R,5R)-2,4-diamino-5-methoxycyclohexyl)-5-hydroxycyclohexanecarboxamide 在 二甲基二硫 、 三氟甲磺酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (2R,3R,5R,6S)-5-azido-2-(azidomethyl)-6-(((1S,2S,4R,5R)-2,4-diazido-5-(((1S,2S,4R,5R)-2,4-diazido-5-methoxycyclohexyl)carbomoyl)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 (2R,3R,5R,6S)-5-azido-2-(azidomethyl)-6-(((1S,2S,4R,5R)-2,4-diazido-5-(((1S,2S,4R,5R)-2,4-diazido-5-methoxycyclohexyl)carbomoyl)cyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  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 triflic azide 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以100 mg的产率得到(1R,2R,4S,5S)-2,4-diazido-N-((1S,2S,4R,5R)-2,4-diamino-5-methoxycyclohexyl)-5-hydroxycyclohexanecarboxamide
  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