N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-[(tert-butoxycarbonyl)amino]-D,L-octadecanamide | 199448-57-2

• 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-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-[(tert-butoxycarbonyl)amino]-D,L-octadecanamide
• CAS: 199448-57-2
• 化学式: C₃₇H₆₄N₂O₁₂
• 分子量: 728.921
• InChiKey: CZOOEDBCYHXFNX-HMZOFHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  51.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-[(tert-butoxycarbonyl)amino]-D,L-octadecanamide 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N-(β-D-glucopyranosyl)-2-amino-D,L-octadecanamide
  参考文献：
  名称：

  Novel Liposaccharide Conjugates for Drug and Peptide Delivery

  摘要：

  Sugar-lipid conjugates with general structure 1-4 were prepared by coupling amino sugars with N-Boc-protected lipoamino acids and oligomers. Conjugates with general structure 5 were also prepared from glucuronic acid and methyl 2-aminohexadecanoate. The physicochemical properties of the conjugates were modified by varying the nature and number of sugars or the number of lipoamino acids or their alkyl chain length. The ability of the liposaccharides to aggregate was examined. These preliminary experiments have demonstrated the ability of the liposaccharides to form particulate systems per se and also their ability to be incorporated into conventional liposomal systems. The structure of the respective liposaccharides and the molar ratio of liposaccharide to dimyristoyl lecithin and cholesterol were found to have a profound effect on the type of colloidal systems produced.

  DOI：

  10.1021/js9702123
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 、 2-((tert-butoxycarbonyl)amino)octadecanoic acid 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以70%的产率得到N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2-[(tert-butoxycarbonyl)amino]-D,L-octadecanamide
  参考文献：
  名称：

  Novel Liposaccharide Conjugates for Drug and Peptide Delivery

  摘要：

  Sugar-lipid conjugates with general structure 1-4 were prepared by coupling amino sugars with N-Boc-protected lipoamino acids and oligomers. Conjugates with general structure 5 were also prepared from glucuronic acid and methyl 2-aminohexadecanoate. The physicochemical properties of the conjugates were modified by varying the nature and number of sugars or the number of lipoamino acids or their alkyl chain length. The ability of the liposaccharides to aggregate was examined. These preliminary experiments have demonstrated the ability of the liposaccharides to form particulate systems per se and also their ability to be incorporated into conventional liposomal systems. The structure of the respective liposaccharides and the molar ratio of liposaccharide to dimyristoyl lecithin and cholesterol were found to have a profound effect on the type of colloidal systems produced.

  DOI：

  10.1021/js9702123