4-acetamidophenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside | 212128-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetamidophenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside
• CAS: 212128-04-6
• 化学式: C₄₂H₃₅NO₁₀S
• 分子量: 745.807
• InChiKey: NCQKLFIHPUMBDB-RUOSMJMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  54.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  143.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-acetamidophenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 、 双丙酮半乳糖 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94%的产率得到1,2:3,4-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-galactopyranose
  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-硝基苯基-β-D-硫代半乳糖苷 在 4-二甲氨基吡啶 、 tin(ll) chloride 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 5.0h， 生成 4-acetamidophenyl 2,3,4,6-tetra-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