2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester | 191331-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester
• CAS: 191331-64-3
• 化学式: C₄₄H₄₉NO₁₅S
• 分子量: 863.937
• InChiKey: AILOLWJXXSNUHS-UEUOLVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  61.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  199.73
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-1-thio-L-fucopyranoside 、 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester 在 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2-(phenylmethoxymethyl)-6-phenylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of sulfo and sialyl LewisX analogs with a mannose at the reducing end

  摘要：

  Stereoselective syntheses of 3-O-sulfo and 3-O-sialyl Lewis(X) analogs 1 and 2 were accomplished. Compound 1 showed greater inhibitory activity than the natural ligand sialyl Lewis(X) against P and L-selectin.

  DOI：

  10.1016/s0960-894x(97)00181-9
• 作为产物：
  描述：

  2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 在 四丁基溴化铵 、 silver trifluoromethanesulfonate 、 三丁基氧化锡 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6S)-3,4,5-triacetoxy-6-[(2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of sulfo and sialyl LewisX analogs with a mannose at the reducing end

  摘要：

  Stereoselective syntheses of 3-O-sulfo and 3-O-sialyl Lewis(X) analogs 1 and 2 were accomplished. Compound 1 showed greater inhibitory activity than the natural ligand sialyl Lewis(X) against P and L-selectin.

  DOI：

  10.1016/s0960-894x(97)00181-9