(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)icos-4-enoxy]oxan-4-yl]-difluoromethyl]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid | 1001846-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)icos-4-enoxy]oxan-4-yl]-difluoromethyl]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1001846-97-4
• 化学式: C₅₆H₁₀₂F₂N₂O₁₅
• 分子量: 1081.43
• InChiKey: TVOZLDRNHKECLP-ZDSYXBFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  75
• 可旋转键数：
  44
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  285
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  在 sodium methylate 、 水 作用下， 以 甲醇 为溶剂， 反应 29.0h， 以2.4 mg的产率得到(2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)icos-4-enoxy]oxan-4-yl]-difluoromethyl]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  Stereocontrolled and Convergent Entry to CF₂-Sialosides:  Synthesis of CF₂-Linked Ganglioside GM4

  摘要：

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

  DOI：

  10.1021/ja075738w