methyl (2S,4S,5R,6R)-5-acetamido-2-(4-tert-butyl-1-hydroxycyclohexyl)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | 773148-50-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,4S,5R,6R)-5-acetamido-2-(4-tert-butyl-1-hydroxycyclohexyl)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 773148-50-8
• 化学式: C₂₂H₃₉NO₉
• 分子量: 461.553
• InChiKey: JKDLPRRBRVQBAK-JXNLSVTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl (2S,4S,5R,6R)-5-acetamido-2-(4-tert-butyl-1-hydroxycyclohexyl)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 作用下， 生成 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(4-tert-butyl-1-hydroxy-cyclohexyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Solid-Phase Chemoenzymatic Synthesis of C-Sialosides

  摘要：

  The chemoenzymatic regioselective acylation of Neu5Ac followed by SmI2-mediated C-glycosylation on a solid support is described for five C-glycosides. This method should facilitate the construction of combinatorial libraries of inhibitors of neuraminidase activity and hemagglutinin interaction as potential antiviral agents.

  DOI：

  10.1021/jo0491298
• 作为产物：
  描述：

  methyl (2S,4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxypropyl]-2,4-dihydroxyoxane-2-carboxylate 在 三氟乙酸 作用下， 反应 0.33h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-2-(4-tert-butyl-1-hydroxycyclohexyl)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Solid-Phase Chemoenzymatic Synthesis of C-Sialosides

  摘要：

  The chemoenzymatic regioselective acylation of Neu5Ac followed by SmI2-mediated C-glycosylation on a solid support is described for five C-glycosides. This method should facilitate the construction of combinatorial libraries of inhibitors of neuraminidase activity and hemagglutinin interaction as potential antiviral agents.

  DOI：

  10.1021/jo0491298