3-[3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyloxy]-5-methoxycarbonylphenoxyacetic acid tert-butyl ester | 206053-76-1

• 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: 3-[3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyloxy]-5-methoxycarbonylphenoxyacetic acid tert-butyl ester
• 英文别名: methyl 3-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]-5-[3-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]propoxy]benzoate
• CAS: 206053-76-1
• 化学式: C₄₄H₅₂O₁₀
• 分子量: 740.891
• InChiKey: XGNPHVSYIMBPLW-FYUBRNRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-[3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyloxy]-5-methoxycarbonylphenoxyacetic acid tert-butyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 13.0h， 生成 {3-(2-Hydroxy-ethylcarbamoyl)-5-[3-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-propoxy]-phenoxy}-acetic acid
  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：

  3,5-二羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-[3-(tri-O-benzyl-α-L-fucopyranosyl)-1-propyloxy]-5-methoxycarbonylphenoxyacetic acid tert-butyl ester
  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

文献信息

• Synthesis of novel Sialyl-LewisX glycomimetics as selectin antagonists
  作者：Gerhard Kretzschmar

  DOI：10.1016/s0040-4020(98)00105-7

  日期：1998.4

  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.