(1R,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexyl acetate | 894423-96-2

• 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-hydroxycyclohexyl acetate
• 英文别名: [(1R,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexyl] acetate
• CAS: 894423-96-2
• 化学式: C₈H₁₂N₆O₃
• 分子量: 240.222
• InChiKey: SDHROQOHVSCAOX-FKSUSPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：

  (1R,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexyl acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 21.0 ℃ 、379.21 kPa 条件下， 反应 5.0h， 以96%的产率得到[(1R,2R,4S,5S)-2,4-diamino-5-hydroxycyclohexyl] acetate
  参考文献：
  名称：

  Enzymatic desymmetrization of 2,5-dideoxystreptamine precursors

  摘要：

  The stereoselective enzymatic acylation of meso-6,7-diazabicyclo[3.2.1]oct-6-ene-2,4-diol 4 and meso-4,6-diazidocyclohexane-1,3-diol 5 in organic media gave the corresponding monoesters in high enantiomeric excess. The hydrolysis of the corresponding diacetate derivatives in the presence of a different set of enzymes provided the same monoesters. The products are precursors of dideoxystreptamine, an aminocyclitol found in synthetic aminoglycoside antibiotics. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.014
• 作为产物：
  描述：

  meso-(1R,3S,4S,6R)-4,6-diazidocyclohexane-1,3-diol 在 4-二甲氨基吡啶 吡啶 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R,4S,5S)-2,4-diazido-5-hydroxycyclohexyl acetate
  参考文献：
  名称：

  胺-叠氮化物相互转化的化学：催化重氮转移和区域选择性叠氮化物还原

  摘要：

  叠氮化物已被证明是有机合成中胺的有用前体。这份报告描述了重氮转移反应的改进和含有多种叠氮化物的化合物的区域选择性叠氮化物还原的第一个例子。使用特定比例的溶剂和氯化锌作为催化剂导致更有效的重氮转移反应，能够以比以前报道的更短的反应时间提供>90% 的转化率/胺。通过在低温下使用三甲基膦对施陶丁格反应进行改进，可以以中等产率以良好的区域选择性还原叠氮化物。电子因素决定叠氮化物还原的选择性，反应可通过起始材料的 NMR 分析进行预测。

  DOI：

  10.1021/ja0264605

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.