4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester | 186585-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester
• 英文别名: benzyl 5-[[(2S,3R)-3-hydroxy-1-[2-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethylamino]-1-oxo-4-phenylmethoxybutan-2-yl]amino]-5-oxopentanoate
• CAS: 186585-61-5
• 化学式: C₅₂H₆₀N₂O₁₀
• 分子量: 873.056
• InChiKey: IBQDUFRVSNDFAO-PQIWTJCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  64
• 可旋转键数：
  26
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 以95%的产率得到4-{(1S,2R)-2,3-Dihydroxy-1-[2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1
• 作为产物：
  描述：

  {(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-{(1S,2R)-3-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester
  参考文献：
  名称：

  C-Fucopeptides as selectin antagonists: Attachment of lipid moieties enhances the activity

  摘要：

  The biological activity of a potent selectin antagonist could be 40-fold enhanced by attachment of a lipid moiety. Also an enantioselective synthesis of beta,omega-dihydroxyamino acids by Sharpless asymmetric dihydroxylation (AD-reaction) allowed general access to this important class of compounds. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02121-1