N-((2S,3R,4S,5S)-3,4,5-tris(benzyloxy)-6-(dodecyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide | 1325147-13-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-((2S,3R,4S,5S)-3,4,5-tris(benzyloxy)-6-(dodecyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide
• CAS: 1325147-13-4
• 化学式: C₉₁H₁₂₅NO₁₁
• 分子量: 1408.99
• InChiKey: WRMOPUZTGQLGTF-CVQBUIJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.14
• 重原子数：
  103.0
• 可旋转键数：
  58.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121.4
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4S,5S)-3,4,5-tris(benzyloxy)-6-(dodecyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 以61%的产率得到N-((2S,3R,4S,5S)-6-(dodecyloxy)-3,4,5-trihydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide
  参考文献：
  名称：

  The Total Synthesis of Immunostimulant α-Galactosylceramides from Naturally Configured α-Galactoside Raffinose

  摘要：

  The total synthesis of absolute anomeric confirmation alpha-galactosylceramide analogues from raffinose is described. Using the naturally occurring alpha-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical alpha-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new alpha-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

  DOI：

  10.1021/ol201695n
• 作为产物：
  描述：

  N-羟基琥珀酰亚胺硬酯酸酯 、 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以1.34 g的产率得到N-((2S,3R,4S,5S)-3,4,5-tris(benzyloxy)-6-(dodecyloxy)-1-((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yloxy)hexan-2-yl)stearamide
  参考文献：
  名称：

  The Total Synthesis of Immunostimulant α-Galactosylceramides from Naturally Configured α-Galactoside Raffinose

  摘要：

  The total synthesis of absolute anomeric confirmation alpha-galactosylceramide analogues from raffinose is described. Using the naturally occurring alpha-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical alpha-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new alpha-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

  DOI：

  10.1021/ol201695n