p-methylphenyl 5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose | 817195-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose
• 英文别名: p-methylphenyl-5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose；[(2R,3R,4R,5S)-2-(azidomethyl)-4-benzoyloxy-5-(4-methylphenyl)sulfanyloxolan-3-yl] benzoate
• CAS: 817195-49-6
• 化学式: C₂₆H₂₃N₃O₅S
• 分子量: 489.552
• InChiKey: RUFSOIRHFORHSP-FCBCXNLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 11.67h， 生成 (2S,3R,4R,5R)-2-(((1S,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-(((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-(acetoxymethyl)-3-azidotetrahydro-2H-pyran-2-yl)oxy)cyclohexyl)oxy)-5-(azidomethyl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  WO2007/113841

  摘要：

  公开号：
• 作为产物：
  描述：

  四乙酰核糖 在 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 p-methylphenyl 5-deoxy-5-azido-2,3-di-O-benzoyl-1-thio-β-D-ribofuranose
  参考文献：
  名称：

  合成氨基糖苷的双重作用：对炭疽芽孢杆菌的抗菌活性和对炭疽致死因子的抑制作用。

  摘要：

  DOI：

  10.1002/anie.200462003

文献信息

• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes
  申请人：Baasov Timor

  公开号：US20050004052A1

  公开（公告）日：2005-01-06

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance.

  一种新型氨基糖苷类药物，与目前已有的氨基糖苷类药物在骨架方面具有一些结构特征，同时又具有显著的结构差异。这种相似性使得这些氨基糖苷类药物具有很高的抗菌作用和有效性，而显著的差异使得这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的发展。
• Highly Efficient <i>O</i>-Glycosylations with <i>p</i>-Tolyl Thioribosides and <i>p</i>-TolSOTf
  作者：Michio Kurosu、Kai Li

  DOI：10.1021/jo801408x

  日期：2008.12.19

  GraphicsA wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.
• Redesign of aminoglycosides for treatment of human genetic diseases caused by premature stop mutations
  作者：Igor Nudelman、Annie Rebibo-Sabbah、Dalia Shallom-Shezifi、Mariana Hainrichson、Ido Stahl、Tamar Ben-Yosef、Timor Baasov

  DOI：10.1016/j.bmcl.2006.09.013

  日期：2006.12

  A series of new derivatives of the clinically used aminoglycoside antibiotic paromomycin were designed, synthesized, and their ability to read-through premature stop codon mutations was examined in both in vitro translation system and ex vivo mammalian cultured cells. One of these structures, a pseudo-trisaccharide derivative, showed notably higher stop codon read-through activity in cultured cells compared to those of paromomycin and gentamicin. (c) 2006 Elsevier Ltd. All rights reserved.
• Preparation and Insecticidal Activity of the First Organofluorine Insecticide Based on β-D-Ribofuranoside Monosaccharide
  作者：V. V. Belakhov、I. V. Boikova、I. L. Krasnobaeva、V. A. Kolodyaznaya

  DOI：10.1134/s1070363221130181

  日期：2021.12
• Dual Effect of Synthetic Aminoglycosides: Antibacterial Activity againstBacillus anthracis and Inhibition of Anthrax Lethal Factor
  作者：Micha Fridman、Valery Belakhov、Lac V. Lee、Fu-Sen Liang、Chi-Huey Wong、Timor Baasov

  DOI：10.1002/anie.200462003

  日期：2005.1.7