methyl 2-[(12-benzyloxycarbonylamino)dodecanoyl]mino-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside | 470665-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-[(12-benzyloxycarbonylamino)dodecanoyl]mino-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside
• CAS: 470665-55-5
• 化学式: C₄₁H₇₀N₂O₉
• 分子量: 735.015
• InChiKey: QAQCUARWKZDACI-HEBMYWSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  52.0
• 可旋转键数：
  30.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  152.65
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[(12-benzyloxycarbonylamino)dodecanoyl]mino-2-deoxy-3-O-tetradecanoyl-α-D-glucopyranoside 在 sodium azide 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 6-azido-2-[(12-benzyloxycarbonylamino)dodecanoyl]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
• 作为产物：
  描述：

  methyl 2-[(12-benzyloxycarbonylamino)dodecanoyl]amino-2-deoxy-4,6-isopropylidene-3-O-tetradecanoyl-α-D-glucopyranoside 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以63%的产率得到methyl 2-[(12-benzyloxycarbonylamino)dodecanoyl]mino-2-deoxy-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