4-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside | 167084-08-4

• 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-1-thio-β-D-galactopyranoside
• 英文别名: p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-d-galactopyranoside；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-(4-nitrophenyl)sulfanyloxan-3-yl] benzoate
• CAS: 167084-08-4
• 化学式: C₃₃H₂₇NO₁₀S
• 分子量: 629.644
• InChiKey: DQGPEFOBMAXYJC-AZLQSNHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  180
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 、 4-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以89%的产率得到4-nitrophenyl O-(3,4-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4

  摘要：

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.

  DOI：

  10.1080/07328309808002341
• 作为产物：
  描述：

  4-硝基苯硫醇 在 吡啶 、 sodium methylate 、 四丁基硫酸氢铵 、 sodium carbonate 、 乙酰氯 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 94.0h， 生成 4-nitrophenyl 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

文献信息

• Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors
  作者：Suoding Cao、Serge J. Meunier、Fredrik O. Andersson、Marie Letellier、René Roy

  DOI：10.1016/s0957-4166(00)86308-9

  日期：1994.11

  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.
• Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4
  作者：Suoding Cao、Fernando Hernández-Matéo、René Roy

  DOI：10.1080/07328309808002341

  日期：1998.5.1

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.