methyl 5-acetamido-2,4,7,8-tetra-O-acetyl-9-O-t.butyldimethylsilyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonate | 139621-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-2,4,7,8-tetra-O-acetyl-9-O-t.butyldimethylsilyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-2,4-diacetyloxy-6-[(1S,2R)-1,2-diacetyloxy-3-[tert-butyl(dimethyl)silyl]oxypropyl]oxane-2-carboxylate
• CAS: 139621-87-7
• 化学式: C₂₆H₄₃NO₁₃Si
• 分子量: 605.712
• InChiKey: TXZXREABPMMHIL-RNCZJOPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  179
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2,4,7,8-tetra-O-acetyl-9-O-t.butyldimethylsilyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonate 在 甲酸 、 四氧化钌 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 84.42h， 生成 methyl (5-acetamido-4,7,9-tri-O-acetyl-2,3,5-trideoxy-2,3-didehydro-β-D-galacto-2,8-nondiulopyranosid)onate
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, 24: Synthesis of the ?-methylketoside of 8-oxo-N-acetylneuraminic acid and related derivatives

  摘要：

  The synthesis of the sodium 5-acetamido-2,3,5-trideoxy-2,3 didehydro-D-galacto-2,8-nondiulopyranosidonate 8,8-dimethyl acetal (8) and of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonate 8,8 dimethyl acetal (11) as well as of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonic acid (12) is reported involving the easily accessible 8-oxo-derivative 5. Compounds 11 and 12, respectively, showed to have glycosidic bond with remarkable stability to acidic conditions.

  DOI：

  10.1007/bf00823430
• 作为产物：
  描述：

  N-乙酰神经氨酸甲酯 在 吡啶 、 咪唑 、 3 A molecular sieve 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 methyl 5-acetamido-2,4,7,8-tetra-O-acetyl-9-O-t.butyldimethylsilyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonate
  参考文献：
  名称：

  Structural variations of N-acetylneuraminic acid, 24: Synthesis of the ?-methylketoside of 8-oxo-N-acetylneuraminic acid and related derivatives

  摘要：

  The synthesis of the sodium 5-acetamido-2,3,5-trideoxy-2,3 didehydro-D-galacto-2,8-nondiulopyranosidonate 8,8-dimethyl acetal (8) and of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonate 8,8 dimethyl acetal (11) as well as of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonic acid (12) is reported involving the easily accessible 8-oxo-derivative 5. Compounds 11 and 12, respectively, showed to have glycosidic bond with remarkable stability to acidic conditions.

  DOI：

  10.1007/bf00823430