perbenzyl-perazido-neamine | 937021-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: perbenzyl-perazido-neamine
• 英文别名: 3',4',5,6-tetra-O-benzyl-1,3,2',6'-tetrazidoneamine；(2R,3R,4R,5R,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)-2-(((1R,2R,3S,4R,6S)-4,6-diazido-2,3-bis(benzyloxy)cyclohexyl)oxy)tetrahydro-2H-pyran；5,6,3',4'-tetra-O-benzyl-1,3,2',6'-teraazidoneamine；(2R,3R,4R,5R,6R)-5-azido-2-(azidomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diazido-2,3-bis(phenylmethoxy)cyclohexyl]oxy-3,4-bis(phenylmethoxy)oxane
• CAS: 937021-95-9
• 化学式: C₄₀H₄₂N₁₂O₆
• 分子量: 786.85
• InChiKey: IULRKMGYNCBTNA-AFFUZZABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  58
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  perbenzyl-perazido-neamine 在 MP-TsOH resin sodium hydroxide 、 水 、 sodium hydride 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-hydroxy-2-[(2R)-2-hydroxy-3-(methylamino)propoxy]cyclohexyl]oxyoxane-3,4-diol
  参考文献：
  名称：

  靶向细菌 rRNA 并抑制耐药酶的双功能抗生素的设计

  摘要：

  DOI：

  10.1021/ja000575w
• 作为产物：
  描述：

  neamine tetrahydrochloride 在 triflic azide 、 sodium hydride 、 copper(II) sulfate 、 三乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 perbenzyl-perazido-neamine
  参考文献：
  名称：

  A Short and Scalable Route to Orthogonally O-Protected 2-Deoxystreptamine

  摘要：

  A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.

  DOI：

  10.1021/jo062369y

文献信息

• Chemo- and Site-Selective Alkyl and Aryl Azide Reductions with Heterogeneous Nanoparticle Catalysts
  作者：Venkatareddy Udumula、S. Hadi Nazari、Scott R. Burt、Madher N. Alfindee、David J. Michaelis

  DOI：10.1021/acscatal.6b01217

  日期：2016.7.1

  to generating new leads for drug discovery. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. The nanoparticle catalysts are highly chemoselective for reduction of alkyl and aryl azides under mild conditions and in the presence of a variety of easily reduced functional groups

  生物活性天然产物的位点选择性修饰是产生用于药物发现的新线索的有效方法。在这里，我们表明，异质纳米颗粒催化剂能够实现聚叠氮化物底物的位点选择性单还原，以生成氨基糖苷类抗生素衍生物。纳米颗粒催化剂在温和条件下和在各种容易还原的官能团存在下对烷基和芳基叠氮化物的还原具有高度的化学选择性。已显示出用于单叠氮化物还原的高区域选择性有利于空间上受阻最小的叠氮化物的还原。我们假设观察到的选择性源自较少受阻的叠氮化物基团与纳米颗粒催化剂表面相互作用的更大能力。
• Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations
  作者：Li-Juan Pang、Dan Wang、Jian Zhou、Li-He Zhang、Xin-Shan Ye

  DOI：10.1039/b907518f

  日期：——

  Neamine is normally found as a core structure of aminoglycoside antibiotics. In order to understand the relationship between the antibiotic activity and the configurations of the functional groups of neamine, a series of novel neamine analogues with functional group manipulations on the 2-deoxystreptamine (2-DOS) ring or the sugar ring were designed and synthesized. The synthetic approach involved

  神经胺通常被认为是氨基糖苷类抗生素的核心结构。为了了解抗生素活性与功能基团的构型之间的关系神经胺，设计并合成了一系列在2-deoxystreptamine（2-DOS）环或糖环上带有官能团的新型Neamine类似物。合成方法涉及通过催化Ferrier II重排，立体和区域选择性官能团转化，糖基偶联反应和整体脱保护来构建2-DOS衍生物。在合成的神经胺类似物中，四种化合物具有可比的16S rRNA结合亲和力，与神经胺，而与18S rRNA的结合亲和力比 神经胺，这意味着对哺乳动物的毒性较低。该策略可能在其他化学合成中具有应用价值。神经胺 衍生物和具有改善的生物活性的新型氨基糖苷类抗生素。
• Investigation of the Regioselectivity for the Staudinger Reaction and Its Application for the Synthesis of Aminoglycosides with N-1 Modification
  作者：Jie Li、Fang-I Chiang、Hsiao-Nung Chen、Cheng-Wei Tom Chang

  DOI：10.1021/jo062588j

  日期：2007.5.1

  The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine and perazidoribostamycin resulting in the synthesis of aminoglycoside antibiotics with activity against drug-resistant bacteria.