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)hexacosanamide | 1325147-12-3

• 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)hexacosanamide
• 英文别名: N-[(2S,3R,4S,5S)-6-dodecoxy-3,4,5-tris(phenylmethoxy)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyhexan-2-yl]hexacosanamide
• CAS: 1325147-12-3
• 化学式: C₉₉H₁₄₁NO₁₁
• 分子量: 1521.21
• InChiKey: FPWZPDRPIRJKIT-IBFPKJILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.3
• 重原子数：
  111
• 可旋转键数：
  66
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  11

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)hexacosanamide 在 10% palladium hydroxide on charcoal 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 以70%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)hexacosanamide
  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-(二十六烷酰氧基)琥珀酰亚胺 、 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以1.33 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)hexacosanamide
  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