(2R,3S,4S,5S,6R)-2-methyl-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(2-hydroxyethyl)tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-3,4,5-triol | 1245811-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5S,6R)-2-methyl-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(2-hydroxyethyl)tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-3,4,5-triol
• 英文别名: (2R,3S,4S,5S,6R)-2-methyl-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(2-hydroxyethyl)oxan-2-yl]methyl]triazol-4-yl]oxan-2-yl]methyl]triazol-4-yl]oxan-2-yl]methyl]triazol-4-yl]oxane-3,4,5-triol
• CAS: 1245811-80-6
• 化学式: C₃₂H₄₉N₉O₁₇
• 分子量: 831.791
• InChiKey: BPJABHQTTXMLJF-FIXAOEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.5
• 重原子数：
  58
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  392
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S,6R)-2-methyl-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(2-hydroxyethyl)tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-3,4,5-triol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以10 mg的产率得到2-[(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-methyloxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]ethyl acetate
  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：

  2-[(2R,3R,4R,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[4-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-methyloxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]triazol-1-yl]methyl]oxan-2-yl]ethyl acetate 在 氨 作用下， 以 甲醇 为溶剂， 以100%的产率得到(2R,3S,4S,5S,6R)-2-methyl-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(2-hydroxyethyl)tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-2-yl]methyl]triazol-4-yl]tetrahydropyran-3,4,5-triol
  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