(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene | 206857-61-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene
• CAS: 206857-61-6
• 化学式: C₇₄H₁₁₁NO₁₄
• 分子量: 1238.69
• InChiKey: LGBOBPUCGTUBIL-RRDDCUSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.59
• 重原子数：
  89.0
• 可旋转键数：
  43.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  180.45
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene 在 苯甲醚 、 三氟乙酸 作用下， 反应 0.25h， 以41%的产率得到(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-dicarboxypropyl)-3-O-benzoyl-β-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 2,6-二叔丁基-4-甲基吡啶 、 硫化氢 、 四丁基氟化铵 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.5h， 生成 (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[2-O-(3,3-di-tert-butyloxycarbonylpropyl)-3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3