3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-1,5-N-(O-tert-butyl-carboxymethyl)imino-1,2,5-trideoxy-D-glucitol | 470665-42-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-1,5-N-(O-tert-butyl-carboxymethyl)imino-1,2,5-trideoxy-D-glucitol
• CAS: 470665-42-0
• 化学式: C₄₁H₄₈N₂O₇
• 分子量: 680.841
• InChiKey: IOFSWKDTRLHFTG-LTPHXHEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.56
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-1,5-N-(O-tert-butyl-carboxymethyl)imino-1,2,5-trideoxy-D-glucitol 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.5h， 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
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 3,4,6-tri-O-benzyl-2-N-benzyloxycarbonylamino-1,2,5-trideoxy-1,5-iminoglucitol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以95%的产率得到3,4,6-tri-O-benzyl-2-[(benzyloxycarbonyl)amino]-1,5-N-(O-tert-butyl-carboxymethyl)imino-1,2,5-trideoxy-D-glucitol
  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