4-sulfamoylbenzoic acid benzyl ether | 100867-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-sulfamoylbenzoic acid benzyl ether
• 英文别名: Benzyl 4-sulfamoylbenzoate
• CAS: 100867-23-0
• 化学式: C₁₄H₁₃NO₄S
• 分子量: 291.328
• InChiKey: XENLMLQJRVBQBR-UHFFFAOYSA-N

物化性质

• 沸点：
  490.4±47.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-sulfamoylbenzoic acid benzyl ether 在 palladium on activated charcoal benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid
  参考文献：
  名称：

  Solid‐Phase Synthesis of Sialyl Tn Antigen

  摘要：

  Solid-phase synthesis of sialyl Tn [alpha-Neu5Ac-(2 -> 6)-alpha-GalNAc-(1 -> O )-Ser] antigen with Kenner's acylsulfonamide linker is described. The acylsulfonamide bond was found to be stable under glycosylation reactions using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter and basic conditions used for the removal of protecting groups. The solid-phase reaction was monitored by the inverse gated decoupling C-13 NMR technique, which enabled quantitative analysis of the reaction progress. At the end of the synthesis, the sulfamyl group of the linker was activated by treatment with (trimethylsilyl)diazomethane to provide a N-methyl-N-acylsulfonamide. The acyl group was displaced with hydroxide to give the corresponding precursors of sialyl Tn antigen and its anomeric isomers, which were deprotected to afford the target molecules.

  DOI：

  10.1080/07328300600778785
• 作为产物：
  描述：

  对羧基苯磺酰胺 、 苯甲醛 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以85%的产率得到4-sulfamoylbenzoic acid benzyl ether
  参考文献：
  名称：

  Solid‐Phase Synthesis of Sialyl Tn Antigen

  摘要：

  Solid-phase synthesis of sialyl Tn [alpha-Neu5Ac-(2 -> 6)-alpha-GalNAc-(1 -> O )-Ser] antigen with Kenner's acylsulfonamide linker is described. The acylsulfonamide bond was found to be stable under glycosylation reactions using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter and basic conditions used for the removal of protecting groups. The solid-phase reaction was monitored by the inverse gated decoupling C-13 NMR technique, which enabled quantitative analysis of the reaction progress. At the end of the synthesis, the sulfamyl group of the linker was activated by treatment with (trimethylsilyl)diazomethane to provide a N-methyl-N-acylsulfonamide. The acyl group was displaced with hydroxide to give the corresponding precursors of sialyl Tn antigen and its anomeric isomers, which were deprotected to afford the target molecules.

  DOI：

  10.1080/07328300600778785

文献信息

• Solid‐Phase Synthesis of Sialyl Tn Antigen
  作者：Takuya Kanemitsu、Shusaku Daikoku、Osamu Kanie

  DOI：10.1080/07328300600778785

  日期：2006.7

  Solid-phase synthesis of sialyl Tn [alpha-Neu5Ac-(2 -> 6)-alpha-GalNAc-(1 -> O )-Ser] antigen with Kenner's acylsulfonamide linker is described. The acylsulfonamide bond was found to be stable under glycosylation reactions using dimethyl(methylthio)sulfonium triflate (DMTST) as a promoter and basic conditions used for the removal of protecting groups. The solid-phase reaction was monitored by the inverse gated decoupling C-13 NMR technique, which enabled quantitative analysis of the reaction progress. At the end of the synthesis, the sulfamyl group of the linker was activated by treatment with (trimethylsilyl)diazomethane to provide a N-methyl-N-acylsulfonamide. The acyl group was displaced with hydroxide to give the corresponding precursors of sialyl Tn antigen and its anomeric isomers, which were deprotected to afford the target molecules.