(2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((1R,2S)-2-acetylamino-2-carboxy-1-methyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 161007-84-7

• 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)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((1R,2S)-2-acetylamino-2-carboxy-1-methyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 161007-84-7
• 化学式: C₃₈H₅₅N₃O₂₃
• 分子量: 921.861
• InChiKey: XFRPSUZBWFZHBF-JSTAHOCUSA-N

物化性质

• 沸点：
  1003.747±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.384±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.39
• 重原子数：
  64.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  345.62
• 氢给体数：
  4.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((1R,2S)-2-acetylamino-2-carboxy-1-methyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以71%的产率得到(2R,4S,5R,6R)-5-Acetylamino-2-[(2R,3R,4R,5R,6S)-5-acetylamino-6-((1R,2S)-2-acetylamino-2-carboxy-1-methyl-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：

  Synthesis of sialyl-Tn antigen. Regioselective sialylation of a galactosamine threonine conjugate unblocked in the carbohydrate portion

  摘要：

  Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.

  DOI：

  10.1016/s0040-4039(00)78495-4
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 在 palladium on activated charcoal 4-二甲氨基吡啶 、 甲酸 、 氢气 、 sodium methylate 、 甲硫基三氟甲烷磺酸酯 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-((1R,2S)-2-acetylamino-2-carboxy-1-methyl-ethoxy)-tetrahydro-pyran-2-ylmethoxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of sialyl-Tn antigen. Regioselective sialylation of a galactosamine threonine conjugate unblocked in the carbohydrate portion

  摘要：

  Regioselective and stereocontrolled formation of the sialyl-Tn antigen conjugate 6 was achieved by reacting the NeuNAc-2-xanthate 2 with the GalNAc threonine acceptor 5 bearing three hydroxy groups. Complete deprotection afforded the sialyl-Tn antigen structure 11.

  DOI：

  10.1016/s0040-4039(00)78495-4