p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-β-D-glucopyranosyl)-β-D-glucopyranoside | 211423-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-β-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(acetylsulfanylmethyl)-6-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-6-(4-methoxyphenoxy)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl] acetate
• CAS: 211423-05-1
• 化学式: C₄₉H₅₁NO₁₆S
• 分子量: 942.007
• InChiKey: YGKSAWYMWQHAKG-YYNJMDKJSA-N

物化性质

• 沸点：
  929.757±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.387±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  67
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  223
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-β-D-glucopyranosyl)-β-D-glucopyranoside 在 双氧水 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 以65%的产率得到p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-acetyl-6-S-acetyl-6-deoxy-6-sulfonato-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Introduction ofC-Sulfonate Groups into Disaccharide Derivatives

  摘要：

  To prepare C-sulfonate derivatives of disaccharides two different strategies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'-C-sulfoaminocellobioside 18 was prepared by construction of the molecule through a glycosylation reaction. In both cases, the synthetic pathway involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.

  DOI：

  10.1080/00397919808004290
• 作为产物：
  描述：

  p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.5h， 生成 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Introduction ofC-Sulfonate Groups into Disaccharide Derivatives

  摘要：

  To prepare C-sulfonate derivatives of disaccharides two different strategies were followed. Thus 6- and 6'-C-sulfocellobiosides 4 and 10-12 were prepared starting from a suitably protected cellobioside. The 6'-C-sulfoaminocellobioside 18 was prepared by construction of the molecule through a glycosylation reaction. In both cases, the synthetic pathway involves regioselective tosylation, introduction of a sulfur atom by nucleophilic displacement with potassium thioacetate and oxidation with hydrogen peroxide.

  DOI：

  10.1080/00397919808004290