N-methyl-N-[O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)oxyethyl]-3,5-bis(octadecyloxy)benzamide | 503306-50-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-methyl-N-[O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)oxyethyl]-3,5-bis(octadecyloxy)benzamide
• CAS: 503306-50-1
• 化学式: C₈₀H₁₁₁NO₁₃
• 分子量: 1294.76
• InChiKey: HXAOUFFPQCOYMB-CBIBEJHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.31
• 重原子数：
  94.0
• 可旋转键数：
  50.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162.43
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N-[O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)oxyethyl]-3,5-bis(octadecyloxy)benzamide 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 以26%的产率得到N-[O-(α-D-mannopyranosyl)oxyethyl]-N-methyl-3,5-bis(octadecyloxy)benzamide
  参考文献：
  名称：

  Facile synthesis of stable lipid analogues possessing a range of alkyl groups: application to artificial glycolipids

  摘要：

  Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An a-mannopyranosyl group was stereoselectively introduced by the conventional imidate method into the terminal hydroxy group without any alternation of other moieties in a molecule. The resulting new glycoconjugates acted as models of natural glycolipids for protein-carbohydrate interactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00266-3
• 作为产物：
  描述：

  硬脂基溴 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 N-methyl-N-[O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)oxyethyl]-3,5-bis(octadecyloxy)benzamide
  参考文献：
  名称：

  Facile synthesis of stable lipid analogues possessing a range of alkyl groups: application to artificial glycolipids

  摘要：

  Efficient preparation of lipid analogues is described in which various long alkoxy chains and 2-hydroxyethyl group were covalently linked with benzoic acid derivatives. An a-mannopyranosyl group was stereoselectively introduced by the conventional imidate method into the terminal hydroxy group without any alternation of other moieties in a molecule. The resulting new glycoconjugates acted as models of natural glycolipids for protein-carbohydrate interactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00266-3