Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((1R,2R)-2-hydroxy-2-m-tolyl-cyclohexyloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 206053-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((1R,2R)-2-hydroxy-2-m-tolyl-cyclohexyloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• 英文别名: Htdhdtvdhnmbok-oclmjhfgsa-；[(2S,3R,4R,5S,6S)-4,5-diacetyloxy-6-[(1R,2R)-2-hydroxy-2-(3-methylphenyl)cyclohexyl]oxy-2-methyloxan-3-yl] acetate
• CAS: 206053-70-5
• 化学式: C₂₅H₃₄O₉
• 分子量: 478.54
• InChiKey: HTDHDTVDHNMBOK-OCLMJHFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((1R,2R)-2-hydroxy-2-m-tolyl-cyclohexyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 17.0h， 生成 {3-[(1R,2R)-1-Hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-benzylsulfanyl}-acetic acid methyl 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
• 作为产物：
  描述：

  (1R,2R)-1-m-Tolyl-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexanol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((1R,2R)-2-hydroxy-2-m-tolyl-cyclohexyloxy)-6-methyl-tetrahydro-pyran-3-yl 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