N-[2-N-(N-(tert-butyloxycarbonyl)-L-leucyl)amino-DL-dodecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine | 1198790-31-6

• 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: N-[2-N-(N-(tert-butyloxycarbonyl)-L-leucyl)amino-DL-dodecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
• CAS: 1198790-31-6
• 化学式: C₃₇H₆₃N₃O₁₃
• 分子量: 757.92
• InChiKey: OZJCOAQVOLLTSZ-IWKCKKAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  53.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  210.96
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-[2-N-(N-(tert-butyloxycarbonyl)-L-leucyl)amino-DL-dodecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到N-[2-(N'-L-leucyl)amino-DL-dodecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Design and synthesis of a series of novel, cationic liposaccharide derivatives as potential penetration enhancers for oral drug delivery

  摘要：

  Oral delivery remains a challenge for a number of drug candidates with low absorption profile (poor membrane permeability, lack of stability, solubility issues or susceptibility to enzymatic degradation) and various methodologies have been investigated to overcome it. The approach presented here consists of associating, by ion-pairing, a hydrophilic, ionizable model drug to a series of synthetic counter-ionic entities with a controlled degree of lipophilicity in order to enhance its penetration of biomembranes and offer some protection against in situ degradation, while preserving its biologically active chemical structure, We report herein the synthesis of a series of positively charged potential penetration enhancers designed from D-glucose, 2-aminododecanoic acid, and additional lipophilic amino acids, and converted afterward into quaternary ammoniums in an optimized, innovative one-step reaction. Each liposaccharide derivative synthesized was fully characterized and their ability to generate micelles in solution was assessed by isothermal titration calorimetry. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.072
• 作为产物：
  描述：

  BOC-L-亮氨酸 、 N-(2-amino-DL-dodecanoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 反应 12.0h， 以65%的产率得到N-[2-N-(N-(tert-butyloxycarbonyl)-L-leucyl)amino-DL-dodecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Design and synthesis of a series of novel, cationic liposaccharide derivatives as potential penetration enhancers for oral drug delivery

  摘要：

  Oral delivery remains a challenge for a number of drug candidates with low absorption profile (poor membrane permeability, lack of stability, solubility issues or susceptibility to enzymatic degradation) and various methodologies have been investigated to overcome it. The approach presented here consists of associating, by ion-pairing, a hydrophilic, ionizable model drug to a series of synthetic counter-ionic entities with a controlled degree of lipophilicity in order to enhance its penetration of biomembranes and offer some protection against in situ degradation, while preserving its biologically active chemical structure, We report herein the synthesis of a series of positively charged potential penetration enhancers designed from D-glucose, 2-aminododecanoic acid, and additional lipophilic amino acids, and converted afterward into quaternary ammoniums in an optimized, innovative one-step reaction. Each liposaccharide derivative synthesized was fully characterized and their ability to generate micelles in solution was assessed by isothermal titration calorimetry. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.072