Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester | 470665-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester
• CAS: 470665-66-8
• 化学式: C₇₈H₁₁₇N₅O₁₃
• 分子量: 1332.81
• InChiKey: OAXIBHZIZGAQOY-VJKSYFQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.68
• 重原子数：
  96.0
• 可旋转键数：
  50.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  221.55
• 氢给体数：
  5.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 以100%的产率得到[(2R,3R,4R,5R,6S)-5-(6-aminohexanoylamino)-2-[[[2-[(2R,3R,4R,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-(tetradecanoylamino)piperidin-1-yl]acetyl]amino]methyl]-3-hydroxy-6-methoxyoxan-4-yl] tetradecanoate
  参考文献：
  名称：

  SYNTHESIS OF PSEUDO-DISACCHARIDE ANALOGUES OF LIPID A: HAPTENS FOR THE GENERATION OF ANTIBODIES WITH GLYCOSIDASE ACTIVITY TOWARDS LIPID A

  摘要：

  In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking the transition state of the,glycosidic hydrolysis, but also a 2-N, 3-O-diacylated glucosamine moiety capable of generating catalytic antibodies with more selective glycosidase properties towards lipid A.

  DOI：

  10.1081/car-120004331
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-2-N-benzyloxycarbonylamino-1,2,5-trideoxy-1,5-iminoglucitol 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.5h， 生成 Tetradecanoic acid (2S,3R,4R,5R,6R)-3-(6-benzyloxycarbonylamino-hexanoylamino)-6-{[2-((2R,3R,4R,5S)-3,4-bis-benzyloxy-2-benzyloxymethyl-5-tetradecanoylamino-piperidin-1-yl)-acetylamino]-methyl}-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  SYNTHESIS OF PSEUDO-DISACCHARIDE ANALOGUES OF LIPID A: HAPTENS FOR THE GENERATION OF ANTIBODIES WITH GLYCOSIDASE ACTIVITY TOWARDS LIPID A

  摘要：

  In order to develop a generic treatment of sepsis caused by infections with Gram-negative bacteria, a series of pseudo-disaccharide analogues of lipid A (1-5) was synthesized. These adducts not only harbor a 2-acylaminodideoxynojirimycin unit mimicking the transition state of the,glycosidic hydrolysis, but also a 2-N, 3-O-diacylated glucosamine moiety capable of generating catalytic antibodies with more selective glycosidase properties towards lipid A.

  DOI：

  10.1081/car-120004331