[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[1-(2-nitrophenyl)triazol-4-yl]propanoylamino]oxan-2-yl]methyl acetate | 1456716-68-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[1-(2-nitrophenyl)triazol-4-yl]propanoylamino]oxan-2-yl]methyl acetate
• CAS: 1456716-68-9
• 化学式: C₂₅H₂₉N₅O₁₂
• 分子量: 591.532
• InChiKey: KIYRYPBALYBWLL-PRDVQWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  220
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[1-(2-nitrophenyl)triazol-4-yl]propanoylamino]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Efficient synthesis of 1,4-disubstituted triazolyl N-carboxamides via a simple and convenient MCR using basic alumina as solid support

  摘要：

  A microwave assisted green protocol for the synthesis of 1,4-disubstituted triazolyl N-carboxamides was explored using basic alumina as solid support. The method allows domino Ullmann-type reaction, Click reaction and formation of ester or amide linkages in a single reaction vessel using Cu(phen)(PPh3)Br and CMPA as catalyst and basic alumina as solid support in high yield. The protocol did not require addition of any external ligands or base. The method was also found to be equally good for the synthesis of bis triazole adducts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.014
• 作为产物：
  描述：

  1-叠氮基-2-硝基苯 在 chloro-phenyl-thio-methylene-dimethylammonium chloride 作用下， 以 氯仿 为溶剂， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[3-[1-(2-nitrophenyl)triazol-4-yl]propanoylamino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Efficient synthesis of 1,4-disubstituted triazolyl N-carboxamides via a simple and convenient MCR using basic alumina as solid support

  摘要：

  A microwave assisted green protocol for the synthesis of 1,4-disubstituted triazolyl N-carboxamides was explored using basic alumina as solid support. The method allows domino Ullmann-type reaction, Click reaction and formation of ester or amide linkages in a single reaction vessel using Cu(phen)(PPh3)Br and CMPA as catalyst and basic alumina as solid support in high yield. The protocol did not require addition of any external ligands or base. The method was also found to be equally good for the synthesis of bis triazole adducts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.014

文献信息

• Synthesis of triazole-fused tetracyclic glycosides in aqueous medium: application of nanodomain cubic cuprous oxide as reusable catalyst in one-pot domino Sonogashira-cyclization
  作者：Nivedita Chatterjee、Rammyani Pal、Swarbhanu Sarkar、Asish Kumar Sen

  DOI：10.1016/j.tetlet.2015.04.106

  日期：2015.6

  An environmentally benign one-pot procedure has been developed for the syntheses of triazole-fused tetracyclic glycosides in aqueous medium. The two step one-pot synthesis involves Sonogashira reaction between azido-alkynes and aryl halides followed by intramolecular 1,3-dipolar cyclization using cubic cuprous oxide nanoparticles as reusable catalyst, under aerobic condition. The method excludes the use of any surfactants or additional ligands as stabilizing agents. The catalyst could be used up to three recycles without any loss of catalytic activity. The method has a broad perspective for the synthesis of medium size ring systems. (C) 2015 Elsevier Ltd. All rights reserved.