methyl 6-amino-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside | 470665-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-amino-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside
• CAS: 470665-65-7
• 化学式: C₄₉H₈₅N₃O₁₀
• 分子量: 876.228
• InChiKey: YLXVMCGJTOKUNV-WQLODKQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  62.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  184.74
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-1,5-N-[carboxymethylimino]-2-(tetradecanoyl)amino-1,2,5-trideoxy-D-glucitol 、 methyl 6-amino-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到
  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：

  methyl 6-azido-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到methyl 6-amino-2-[(R)-3-(6-benzyloxycarbonylamino)hexanoyloxytetradecanoyl]amino-2,6-dideoxy-3-O-tetradecanoyl-α-D-glucopyranoside
  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