(2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester | 146788-04-7

• 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-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 146788-04-7
• 化学式: C₂₁H₂₈FNO₈S
• 分子量: 473.52
• InChiKey: PKAIWWWUYYUZMX-ZOHBSTTGSA-N

物化性质

• 沸点：
  659.9±55.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.76
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123.55
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2-fluoro-4-hydroxy-3-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 溶剂黄146 作用下， 反应 13.0h， 生成 (2R,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-6-((1R,2R)-1,3-diacetoxy-2-hydroxy-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：

  5-(乙酰氨基)-2-氯-2,5-二脱氧-3-S-苯基-3-硫代-D-赤式-alpha-L-葡糖-2-吡喃壬酮糖酸甲酯4,7,8,9-四乙酸酯 在 disodium hydrogenphosphate 、 Dowex 50Wx₈ (H(+)-form) 、 potassium tert-butylate 、 silver trifluoromethanesulfonate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.5h， 生成 (2R,3S,4R,5R,6R)-5-Acetylamino-6-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-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