[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[6-[2,3-di(tetradecoxy)propyl-(4-nitrophenyl)sulfonylamino]hexoxy]oxan-2-yl]methyl acetate | 1235550-12-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[6-[2,3-di(tetradecoxy)propyl-(4-nitrophenyl)sulfonylamino]hexoxy]oxan-2-yl]methyl acetate
• CAS: 1235550-12-5
• 化学式: C₅₇H₉₈N₂O₁₆S
• 分子量: 1099.47
• InChiKey: IFXAIGHDSCZRPN-AOBFICNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  76
• 可旋转键数：
  50
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  234
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[6-[2,3-di(tetradecoxy)propyl-(4-nitrophenyl)sulfonylamino]hexoxy]oxan-2-yl]methyl acetate 在 4-二甲氨基吡啶 、 10% palladium on activated charcoal 、 甲酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 4-[4-[2,3-di(tetradecoxy)propyl-[6-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyhexyl]sulfamoyl]anilino]-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and transfection activity of novel galactosylated polycationic lipid

  摘要：

  In this study, we synthesized a new galactosylated cationic lipid and investigated its biological activity. The structure of lipid combines both spermine residue for DNA compaction and galactose moiety for the improvement of aggregation behavior of lipoplexes. Lipid was low toxic for different mammalian cells, and was able both to compact plasmid DNA and to mediate cellular accumulation of various nucleic acids (ODN, pDNA and siRNA) exhibiting biological activity (transgene expression, gene silencing). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.056
• 作为产物：
  描述：

  6-氨基-1-己醇 在 无水碳酸镉 、 四丁基碘化铵 、 caesium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 45.5h， 生成 [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[6-[2,3-di(tetradecoxy)propyl-(4-nitrophenyl)sulfonylamino]hexoxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Synthesis and transfection activity of novel galactosylated polycationic lipid

  摘要：

  In this study, we synthesized a new galactosylated cationic lipid and investigated its biological activity. The structure of lipid combines both spermine residue for DNA compaction and galactose moiety for the improvement of aggregation behavior of lipoplexes. Lipid was low toxic for different mammalian cells, and was able both to compact plasmid DNA and to mediate cellular accumulation of various nucleic acids (ODN, pDNA and siRNA) exhibiting biological activity (transgene expression, gene silencing). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.056