benzyl (3S)-3-[[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoyl]amino]-4-oxo-4-[5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoate | 463313-66-8

• 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: benzyl (3S)-3-[[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoyl]amino]-4-oxo-4-[5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoate
• CAS: 463313-66-8
• 化学式: C₅₈H₈₄N₄O₂₇
• 分子量: 1269.32
• InChiKey: AYULKGQLLYOJHY-QBKHWZMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  89
• 可旋转键数：
  45
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  399
• 氢给体数：
  4
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  benzyl (3S)-3-[[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoyl]amino]-4-oxo-4-[5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoate 在 三氟乙酸 、 氨 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 26.0h， 以95%的产率得到(S)-3-{(S)-3-Amino-3-[5-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentylcarbamoyl]-propionylamino}-N-[5-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentyl]-succinamic acid
  参考文献：
  名称：

  Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

  摘要：

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00212-4
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 benzyl (3S)-3-[[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-[5-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoyl]amino]-4-oxo-4-[5-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxypentylamino]butanoate
  参考文献：
  名称：

  Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

  摘要：

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00212-4