N-((2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide | 1058144-10-7

• 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,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide
• CAS: 1058144-10-7
• 化学式: C₉₀H₁₅₁NO₉Si₂
• 分子量: 1447.36
• InChiKey: HPJYBSPOJHWLRR-XFOOOPCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.44
• 重原子数：
  102.0
• 可旋转键数：
  60.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  102.94
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-((2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到
  参考文献：
  名称：

  Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

  摘要：

  KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.036
• 作为产物：
  描述：

  N-((2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-hydroxyoctadecan-2-yl)hexacosanamide 、 [(2R,3R,4S,5S,6R)-3,4,5-三苄氧基-6-(苄氧基甲基)四氢吡喃-2-基]2,2,2-三氯乙亚氨酸酯 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以48%的产率得到N-((2S,3R,4R)-3,4-bis((tert-butyldimethylsilyl)oxy)-1-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide
  参考文献：
  名称：

  Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

  摘要：

  KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined. Crown copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.036