N-((2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-oxooctadecan-2-yl)hexacosanamide | 1238214-23-7

• 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-((2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-oxooctadecan-2-yl)hexacosanamide
• CAS: 1238214-23-7
• 化学式: C₅₆H₁₁₅NO₄Si₂
• 分子量: 922.704
• InChiKey: YIFYRTGJJJGOFH-JVDXJGRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.92
• 重原子数：
  63.0
• 可旋转键数：
  45.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-((2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-oxooctadecan-2-yl)hexacosanamide 、 O-(β-D-galactopyranosyl)hydroxylamine 在 盐酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 以34%的产率得到O-β-D-galacopyranosyl-(1',1)-(2S,3S,4R)-2-hexacosanoylamino-3,4-bis(tert-butyldimethylsiloxy)octadecanylaldoxime
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045
• 作为产物：
  描述：

  (2S,3S,4R)-3,4-二[(叔-丁基二甲基硅烷基)氧基]-2-二十六烷酰基氨基-4-十八烷醇 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到N-((2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-oxooctadecan-2-yl)hexacosanamide
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045