2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide | 914097-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide
• CAS: 914097-82-8
• 化学式: C₆₉H₆₆Cl₃NO₂₃S
• 分子量: 1415.7
• InChiKey: NMNBVJOYGZTXPL-NBHXFSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  97.0
• 可旋转键数：
  23.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  291.02
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide 、 (2S,3R,4E)-2-azido-3-(4-methoxybenzyl)-4-octadecen-1,3-diol 在 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl-(1,1)-(2S,3R,4E)-2-azido-3-O-(4-methoxybenzyl)-4-octadecene-1,3-diol
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b
• 作为产物：
  描述：

  在 三乙基硅烷 、 四(三苯基膦)钯 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 2-O-(4-methoxybenzyl)-3,4,6-tri-O-acetyl-α-D-galactopyranosyl-(1,3)-2-O-benzoyl-3-thio-3-deoxy-4,6-O-benzylidene-β-D-galactopyranosyl-(1,4)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl-trichloroacetimide
  参考文献：
  名称：

  Thio-isoglobotrihexosylceramide, an Agonist for Activating Invariant Natural Killer T Cells

  摘要：

  Thio-isoglobotrihexosylceramide (S-iGb3) might be resistant to alpha-galactosidases in antigen-presenting cells and have a longer retaining time in the lysosome before being loaded to CD1d. The biological assay showed that S-iGb3 demonstrates a much higher increase as a stimulatory ligand toward invariant natural killer T (iNKT) cells as compared to iGb3.

  DOI：

  10.1021/ol062199b