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 | 771577-91-4

• 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-6-[(1R,2R)-1,2-dihydroxy-3-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxypropyl]-2,4-dihydroxyoxane-2-carboxylate
• CAS: 771577-91-4
• 化学式: C₂₆H₃₈N₂O₁₂
• 分子量: 570.594
• InChiKey: RTXCSNXEENURLE-HDNBNLMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  210
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  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 吡啶 、 三氟乙酸 作用下， 反应 0.33h， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-hydroxy-1,3-diphenylpropan-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 作用下， 反应 168.0h， 生成 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
  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

文献信息

• Solid-Phase Chemoenzymatic Synthesis of <i>C</i>-Sialosides
  作者：Sultan N. Baytas、Qun Wang、Nathalie A. Karst、Jonathan S. Dordick、Robert J. Linhardt

  DOI：10.1021/jo0491298

  日期：2004.10.1

  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.