(2R,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid | 914801-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
• CAS: 914801-05-1
• 化学式: C₃₉H₅₃N₅O₁₇
• 分子量: 863.873
• InChiKey: VPHHEBIZHDMNSM-PVUKWCIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  327.09
• 氢给体数：
  8.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 (2R,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-amino-6-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic 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：

  N-(tert-butoxycarbonyl)-O-[1-13C]acetyl-L-seryl-4-sulfamoylbenzoic acid 、 、 phenyl 6-O-[1-13C]acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-1-thio-D-galactopyranoside 以25%的产率得到(2S,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-azido-3,4-bis-benzyloxy-6-((S)-2-tert-butoxycarbonylamino-2-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic 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