N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid benzyl ester | 914800-93-4

• 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: N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid benzyl ester
• CAS: 914800-93-4
• 化学式: C₂₄H₂₈N₂O₉S
• 分子量: 521.549
• InChiKey: LLRSBORJLSGCAF-BPFPZANSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  154.17
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以88%的产率得到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：

  BOC-L-丝氨酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid benzyl ester
  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