| 1200132-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1200132-62-2
• 化学式: C₃₂H₃₅N₃O₅
• 分子量: 541.647
• InChiKey: YSJDJNLFBMJTHF-JQWMYKLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol 、 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以89%的产率得到3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-C-[2-(2-hydroxy)propyl]-8-[4-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-1H-1,2,3-triazol-1-yl]-D-glycero-D-talo-oct-1-ynitol
  参考文献：
  名称：

  Modular Approach to Triazole-Linked 1,6-α-d-Oligomannosides to the Discovery of Inhibitors of Mycobacterium tuberculosis Cell Wall Synthetase

  摘要：

  Aiming at developing inhibitors of mannosyltransferases, the enzymes that participate in the biosynthesis of the cell envelope of Mycobacterium tuberculosis, the synthesis of a range of designed triazole-linked 1,6-oligomannosides up to a hexadecamer has been accomplished by a modular approach centered on the Cu(I)-catalyzed azide-alkyne cycloaddition as key process. The efficiency and fidelity of the cycloaddition are substantiated by high yields (76-96%) and exclusive formation of the expected 1,4-disubstituted triazole ring in all oligomer assembling reactions. Key features of oligomers thus prepared are the anomeric carbon-carbon bond of all mannoside residues and the 6-deoxymannoside capping residue. Suitable bioassays with dimer, tetramer, hexamer, octamer, decamer, and hexadecamer showed variable inhibitor activity against mycobacterial alpha-(1,6)-mannosyltransferases, the highest activity (IC50 = 0.14-0.22 mM) being registered with the hexamannoside and octamannoside.

  DOI：

  10.1021/jo100928g
• 作为产物：
  描述：

  在 sodium azide 作用下， 生成
  参考文献：
  名称：

  Modular Approach to Triazole-Linked 1,6-α-d-Oligomannosides to the Discovery of Inhibitors of Mycobacterium tuberculosis Cell Wall Synthetase

  摘要：

  Aiming at developing inhibitors of mannosyltransferases, the enzymes that participate in the biosynthesis of the cell envelope of Mycobacterium tuberculosis, the synthesis of a range of designed triazole-linked 1,6-oligomannosides up to a hexadecamer has been accomplished by a modular approach centered on the Cu(I)-catalyzed azide-alkyne cycloaddition as key process. The efficiency and fidelity of the cycloaddition are substantiated by high yields (76-96%) and exclusive formation of the expected 1,4-disubstituted triazole ring in all oligomer assembling reactions. Key features of oligomers thus prepared are the anomeric carbon-carbon bond of all mannoside residues and the 6-deoxymannoside capping residue. Suitable bioassays with dimer, tetramer, hexamer, octamer, decamer, and hexadecamer showed variable inhibitor activity against mycobacterial alpha-(1,6)-mannosyltransferases, the highest activity (IC50 = 0.14-0.22 mM) being registered with the hexamannoside and octamannoside.

  DOI：

  10.1021/jo100928g

文献信息

• Studies Toward the Synthesis of Inhibitors of Mycobacterium tuberculosis Cell-Wall Biosynthesis: The Assembly of Triazole-Linked 1,6-α-d-Oligomannosides via Click CuAAC
  作者：Alberto Marra、Alessandro Dondoni、Mauro Lo Conte、Angela Chambery

  DOI：10.1055/s-0029-1217751

  日期：2009.10

  A versatile synthesis of 1,6-α-d-oligomannosides featuring the 1,4-disubstituted triazole ring as interglycosidic tether is presented via iterative copper(I)-catalyzed azide-alkyne cycloaddition. Free hydroxy hexamannoside and decamannoside featuring a capping 6-deoxymannose fragment have been prepared and characterized.

  通过铜（I）催化的叠氮-炔烃的迭代环加成反应，制备了以1,4-二取代三唑环为糖苷键的多功能1,6-α-二甘露糖苷。制备了具有封端6-脱氧甘露糖片段的游离羟基六甘露糖苷和十甘露糖苷，并对其进行了表征。