{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 | 206053-92-1

• 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-(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
• 英文别名: 2-[3-(2-hydroxyethylcarbamoyl)-5-[3-[(2S,3R,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]propoxy]phenoxy]acetic acid
• CAS: 206053-92-1
• 化学式: C₄₁H₄₇NO₁₀
• 分子量: 713.825
• InChiKey: RNQLGNNSSNSCJJ-JFZNRXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {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 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 2.0h， 以71%的产率得到2-[3-(2-hydroxyethylcarbamoyl)-5-[3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-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：

  methyl 3-(2-tert-butoxy-2-oxoethoxy)-5-hydroxybenzoate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 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

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.