N-((2S,3S,4R)-1-(((2S,3R,4S,5R,6R)-6-(aminomethyl)-4,5-dihydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxyoctadecan-2-yl)octanamide | 1070774-32-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: N-((2S,3S,4R)-1-(((2S,3R,4S,5R,6R)-6-(aminomethyl)-4,5-dihydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxyoctadecan-2-yl)octanamide
• CAS: 1070774-32-1
• 化学式: C₃₈H₇₄N₂O₁₃
• 分子量: 767.011
• InChiKey: LMBBAOMEMPTEIF-ISBBIDRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  53.0
• 可旋转键数：
  29.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  253.88
• 氢给体数：
  10.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3S,4R)-1-(((2S,3R,4S,5R,6R)-6-(aminomethyl)-4,5-dihydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxyoctadecan-2-yl)octanamide 、 溶剂黄146 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以5.4 mg的产率得到N-[(2S,3S,4R)-1-[(2S,3R,4S,5R,6R)-6-(acetamidomethyl)-4,5-dihydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoctadecan-2-yl]octanamide
  参考文献：
  名称：

  Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties

  摘要：

  Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6 '' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6 '' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.067
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(azidomethyl)-6-(((2S,3S,4R)-3,4-diacetoxy-2-octanamidooctadecyl)oxy)-5-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-((2S,3S,4R)-1-(((2S,3R,4S,5R,6R)-6-(aminomethyl)-4,5-dihydroxy-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxyoctadecan-2-yl)octanamide
  参考文献：
  名称：

  Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties

  摘要：

  Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6 '' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6 '' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.067