(2R,3S,4R,5R,6R)-5-Acetylamino-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester | 183019-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-Acetylamino-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 183019-39-8
• 化学式: C₂₅H₂₈FNO₉S
• 分子量: 537.563
• InChiKey: NOEUMXFECAGJHQ-XCKJJUQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  151.62
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (2R,3S,4R,5R,6R)-5-Acetylamino-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以48%的产率得到(2R,3S,4R,5S,6R)-5-Acetylamino-4-benzoyloxy-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Simple Construction of Neu5Ac(α2-8)Neu5Ac and Total Synthesis of Ganglioside GD₃

  摘要：

  Glycosylation of an 8-unprotected sialyl fluoride 16 with 2 beta-chloro-3 beta-phenylthio-Neu5Ac 2 gave the desired alpha-disialate 23. Subsequent glycosylation of a thiolactoside 19 with the disialyl fluoride 23 gave the tetrasaccharide 28. Synthesis of GD(3) 1 was realized by condensation of the tetrasaccharide 28 with azidosphingosine 31, following our previously reported GM(3) synthesis procedure.

  DOI：

  10.1080/07328309608005696
• 作为产物：
  描述：

  (3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 potassium tert-butylate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2R,3S,4R,5R,6R)-5-Acetylamino-6-((1R,2R)-3-benzoyloxy-1,2-dihydroxy-propyl)-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Simple Construction of Neu5Ac(α2-8)Neu5Ac and Total Synthesis of Ganglioside GD₃

  摘要：

  Glycosylation of an 8-unprotected sialyl fluoride 16 with 2 beta-chloro-3 beta-phenylthio-Neu5Ac 2 gave the desired alpha-disialate 23. Subsequent glycosylation of a thiolactoside 19 with the disialyl fluoride 23 gave the tetrasaccharide 28. Synthesis of GD(3) 1 was realized by condensation of the tetrasaccharide 28 with azidosphingosine 31, following our previously reported GM(3) synthesis procedure.

  DOI：

  10.1080/07328309608005696