(S)-2-{(2R,3S,4S,5R,6R)-2-Aminomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid | 757932-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-{(2R,3S,4S,5R,6R)-2-Aminomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid
• CAS: 757932-28-8
• 化学式: C₂₇H₄₁NO₁₂
• 分子量: 571.622
• InChiKey: MWXGJLPNACPWHD-NNIOFZNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  210.62
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (S)-2-{(2R,3S,4S,5R,6R)-2-Aminomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid 在 sodium hydroxide 作用下， 反应 3.0h， 以85%的产率得到(S)-2-{(2R,3S,4S,5R,6R)-2-(Benzoylamino-methyl)-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid
  参考文献：
  名称：

  Synthesis of sialyl lewisx mimics. Modifications of the 6-position of galactose

  摘要：

  Seven sLe(x) mimics where the -CH2OH group of the galactose moiety is replaced by -CH2NH3+, -CH2NHAc, -CH(2)NHBz, -CH2OSO3Na, -COONa and -CONH2 have been prepared and tested for their binding affinity to E-selectin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00692-2
• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol 在 palladium dihydroxide 吡啶 、 sodium azide 、 ammonium cerium(IV) nitrate 、 氢气 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 149.0h， 生成 (S)-2-{(2R,3S,4S,5R,6R)-2-Aminomethyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid
  参考文献：
  名称：

  Synthesis of sialyl lewisx mimics. Modifications of the 6-position of galactose

  摘要：

  Seven sLe(x) mimics where the -CH2OH group of the galactose moiety is replaced by -CH2NH3+, -CH2NHAc, -CH(2)NHBz, -CH2OSO3Na, -COONa and -CONH2 have been prepared and tested for their binding affinity to E-selectin. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00692-2