methyl 6-deoxy-6-[[(1-fluorenylmethoxycarbonyl)-2-pyrrolidinyl]carbonylamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside | 1115270-72-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 6-deoxy-6-[[(1-fluorenylmethoxycarbonyl)-2-pyrrolidinyl]carbonylamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside
• CAS: 1115270-72-8
• 化学式: C₅₅H₈₈N₂O₈
• 分子量: 905.312
• InChiKey: HDOFKFDSJBMTLO-YQLPNJNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  65.0
• 可旋转键数：
  34.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  115.79
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-[[(1-fluorenylmethoxycarbonyl)-2-pyrrolidinyl]carbonylamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到methyl 6-deoxy-6-[(-2-pyrrolidinyl)carbonylamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  Glycolipids and Benzylammonium Lipids as Novel Antisepsis Agents: Synthesis and Biological Characterization

  摘要：

  New glycolipids and a benzylammonium lipid were rationally designed by varying the chemical structure of a D-glucose-derived hit compound active as lipid A antagonist. We report the synthesis of these compounds, their in vitro activity as lipid A antagonists on HEK cells, and the capacity to inhibit LPS-induced septic shock in vivo. The lack of toxicity and the good in vivo activity suggest the use of some compounds of the panel as hits for antisepsis drug development.

  DOI：

  10.1021/jm801333m
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(氨基甲基)-6-甲氧基-4,5-双(十四烷氧基)四氢-2H-吡喃-3-醇 、 Fmoc-L-脯氨酸 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以90%的产率得到methyl 6-deoxy-6-[[(1-fluorenylmethoxycarbonyl)-2-pyrrolidinyl]carbonylamino]-2,3-di-O-tetradecyl-α-D-glucopyranoside
  参考文献：
  名称：

  Glycolipids and Benzylammonium Lipids as Novel Antisepsis Agents: Synthesis and Biological Characterization

  摘要：

  New glycolipids and a benzylammonium lipid were rationally designed by varying the chemical structure of a D-glucose-derived hit compound active as lipid A antagonist. We report the synthesis of these compounds, their in vitro activity as lipid A antagonists on HEK cells, and the capacity to inhibit LPS-induced septic shock in vivo. The lack of toxicity and the good in vivo activity suggest the use of some compounds of the panel as hits for antisepsis drug development.

  DOI：

  10.1021/jm801333m