3,4,6-tri-O-benzyl-1,5-N-[(O-tert-butyl-carboxymethyl)imino]-2-(tetradecanoyl)amino-1,2,5-trideoxy-D-glucitol | 470665-44-2

• 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-1,5-N-[(O-tert-butyl-carboxymethyl)imino]-2-(tetradecanoyl)amino-1,2,5-trideoxy-D-glucitol
• CAS: 470665-44-2
• 化学式: C₄₇H₆₈N₂O₆
• 分子量: 757.067
• InChiKey: IBSJBBWRUYZDOI-QQEKSHBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  55.0
• 可旋转键数：
  25.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  86.33
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,5-N-[(O-tert-butyl-carboxymethyl)imino]-2-(tetradecanoyl)amino-1,2,5-trideoxy-D-glucitol 在 三氟乙酸 作用下， 反应 2.0h， 以100%的产率得到3,4,6-tri-O-benzyl-1,5-N-[carboxymethylimino]-2-(tetradecanoyl)amino-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
• 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 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 17.5h， 生成 3,4,6-tri-O-benzyl-1,5-N-[(O-tert-butyl-carboxymethyl)imino]-2-(tetradecanoyl)amino-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