3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-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 | 1245811-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-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
• 英文别名: [(2R,3R,4R,5R,6R)-6-[1-[[(2R,3R,4R,5R,6R)-6-ethynyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]triazol-4-yl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 1245811-67-9
• 化学式: C₅₈H₅₉N₃O₉
• 分子量: 942.121
• InChiKey: ZFFOALQRGXIEJA-DZJRUJPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  70
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-[1-(6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosyl)-1H-1,2,3-triazol-4-yl]-3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-1-O-methoxymethyl-D-glycero-D-talo-octitol 、 3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-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 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， 生成 [(2R,3R,4R,5R,6R)-6-[1-[[(2R,3R,4S,5R,6R)-6-[1-[[(2R,3R,4S,5R,6R)-6-[1-[[(2R,3R,4R,5R,6R)-6-[2-(methoxymethoxy)ethyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]triazol-4-yl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]triazol-4-yl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl]triazol-4-yl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
  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：

  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 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以92%的产率得到3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-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

文献信息

• Modular Approach to Triazole-Linked 1,6-α-<scp>d</scp>-Oligomannosides to the Discovery of Inhibitors of <i>Mycobacterium tuberculosis</i> Cell Wall Synthetase
  作者：Mauro Lo Conte、Alberto Marra、Angela Chambery、Sudagar S. Gurcha、Gurdyal S. Besra、Alessandro Dondoni

  DOI：10.1021/jo100928g

  日期：2010.10.1

  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.