(1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(2,2-dimethoxycarbonyl-1-ethyl)phenyl]cyclohexane | 206053-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(2,2-dimethoxycarbonyl-1-ethyl)phenyl]cyclohexane
• 英文别名: Zhxiqpbbnzgums-blmiivjusa-；dimethyl 2-[[3-[(1R,2R)-1-hydroxy-2-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxycyclohexyl]phenyl]methyl]propanedioate
• CAS: 206053-68-1
• 化学式: C₄₅H₅₂O₁₀
• 分子量: 752.902
• InChiKey: ZHXIQPBBNZGUMS-BLMIIVJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(2,2-dimethoxycarbonyl-1-ethyl)phenyl]cyclohexane 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 生成 (1R,2R)-1,2-dihydroxy-2-O-(α-L-fucopyranosyl)-1-[3-(2,2-dicarboxy-1-ethyl)phenyl]cyclohexane
  参考文献：
  名称：

  Synthesis of novel Sialyl-LewisX glycomimetics as selectin antagonists

  摘要：

  A series of low molecular weight sialyl-Lewis(X) analogs based on either rigid or flexible replacements for the carbohydrates were designed as orally available anti-inflammatory drugs, synthesized and tested in cell-based adhesion assays. The flexible glycomimetic 7a lacking any glycoside or peptide linkage was prepared in 4 steps and 41% overall yield from methyl 3,5-dihydroxybenzoate and the fucose derivative 18 and exhibited about equal binding affinity to E-and P-selectin compared to the parent tetrasaccharide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00105-7
• 作为产物：
  描述：

  (1R,2R)-2-acetoxy-1-hydroxy-1-[3-(2,2-diethoxycarbonyl-1-ethyl)phenyl]cyclohexane 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 (1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(2,2-dimethoxycarbonyl-1-ethyl)phenyl]cyclohexane
  参考文献：
  名称：

  Synthesis of novel Sialyl-LewisX glycomimetics as selectin antagonists

  摘要：

  A series of low molecular weight sialyl-Lewis(X) analogs based on either rigid or flexible replacements for the carbohydrates were designed as orally available anti-inflammatory drugs, synthesized and tested in cell-based adhesion assays. The flexible glycomimetic 7a lacking any glycoside or peptide linkage was prepared in 4 steps and 41% overall yield from methyl 3,5-dihydroxybenzoate and the fucose derivative 18 and exhibited about equal binding affinity to E-and P-selectin compared to the parent tetrasaccharide. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00105-7