methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-(2-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | 773148-48-4

• 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-4-hydroxy-2-(2-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 773148-48-4
• 化学式: C₂₂H₃₇NO₉
• 分子量: 459.537
• InChiKey: MNWSNTBFQRCXMF-AGJWBHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• 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-4-hydroxy-2-(2-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 作用下， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]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
• 作为产物：
  描述：

  N-acetyl neuraminic acid 在 吡啶 、 4 A molecular sieve 、 Amberlist H⁽¹⁺⁾ resin 、 subtilisin Carlsberg ChiroCLEC-BL 、 三氟乙酸 作用下， 反应 168.33h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-hydroxy-2-(2-hydroxy-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl)-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