(1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(4-methoxycarbonylpiperidin-1-ylmethyl)phenyl]cyclohexane | 206053-78-3

• 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-(4-methoxycarbonylpiperidin-1-ylmethyl)phenyl]cyclohexane
• 英文别名: Gikabkjeqgtqhm-zimpswdqsa-；methyl 1-[[3-[(1R,2R)-1-hydroxy-2-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxycyclohexyl]phenyl]methyl]piperidine-4-carboxylate
• CAS: 206053-78-3
• 化学式: C₄₇H₅₇NO₈
• 分子量: 763.971
• InChiKey: GIKABKJEQGTQHM-ZIMPSWDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  9

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-(4-methoxycarbonylpiperidin-1-ylmethyl)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-(4-carboxypiperidin-1-ylmethyl)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)-1-(3-methylphenyl)cyclohexane-1,2-diol 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 potassium carbonate 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (1R,2R)-1,2-dihydroxy-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-[3-(4-methoxycarbonylpiperidin-1-ylmethyl)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