4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-galactopyranoside | 167084-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-nitrophenyl)sulfanyloxan-3-yl] benzoate
• CAS: 167084-07-3
• 化学式: C₃₉H₄₁NO₁₀SSi
• 分子量: 743.907
• InChiKey: VJIQLYJRLZRTCS-NNQVOBLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 乙酰氯 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.25h， 生成 4-nitrophenyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors

  摘要：

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.

  DOI：

  10.1016/s0957-4166(00)86308-9
• 作为产物：
  描述：

  4-硝基苯基-β-D-硫代半乳糖苷 在 吡啶 作用下， 反应 8.5h， 生成 4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-t-butyldimethylsilyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors

  摘要：

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.

  DOI：

  10.1016/s0957-4166(00)86308-9