Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-ethoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester | 182865-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-ethoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS: 182865-93-6
• 化学式: C₃₈H₅₅NO₂₃
• 分子量: 893.848
• InChiKey: TVFLMWHWFDLGFF-NYCNYBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  62.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  294.88
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-ethoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到N-[(2R,3R,4R,5S,6R)-2-Ethoxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Stereoselective synthesis of lewis-associated trisaccharides as E-selectin inhibitors

  摘要：

  Three types of Lewis-associated trisaccharides [the Le(a) analogs, their epimers with respect to the fucose residue (the 1c-epi-Le(a) analogs), and the Le(X) analogs] were synthesized in a stereoselective manner. Not only the Le(a) analogs but also the 1c-epi-Le(a) analogs inhibited E-selectin-mediated neutrophil accumulation into pleural cavity in lipoteichoic acid-treated mice, with the trend being Le(a) > 1c-epi-Le(a) > Le(X). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00370-8
• 作为产物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-allyloxycarbonylamino-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 tin(II) trifluoromethanesulfonate 、 四(三苯基膦)钯 、 polymethylhydrosiloxane 、 1,1-二氯甲醚 、 甲酸铵 、 silver perchlorate 、 碳酸氢钠 、 1,1,3,3-四甲基脲 、 tin(ll) chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-ethoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of lewis-associated trisaccharides as E-selectin inhibitors

  摘要：

  Three types of Lewis-associated trisaccharides [the Le(a) analogs, their epimers with respect to the fucose residue (the 1c-epi-Le(a) analogs), and the Le(X) analogs] were synthesized in a stereoselective manner. Not only the Le(a) analogs but also the 1c-epi-Le(a) analogs inhibited E-selectin-mediated neutrophil accumulation into pleural cavity in lipoteichoic acid-treated mice, with the trend being Le(a) > 1c-epi-Le(a) > Le(X). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00370-8