methyl (5-acetamido-4,7-di-O-acetyl-2,3,5-trideoxy-2,3-didehydro-β-D-galacto-2,8-nondiulopyranosid)onate 8,8-dimethylacetal | 139621-94-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (5-acetamido-4,7-di-O-acetyl-2,3,5-trideoxy-2,3-didehydro-β-D-galacto-2,8-nondiulopyranosid)onate 8,8-dimethylacetal
• 英文别名: methyl (2R,3R,4S)-3-acetamido-4-acetyloxy-2-[(1S)-1-acetyloxy-3-hydroxy-2,2-dimethoxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 139621-94-6
• 化学式: C₁₈H₂₇NO₁₁
• 分子量: 433.412
• InChiKey: AOUGWJDTZPWAQJ-XZDPQHSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  methyl (5-acetamido-4,7,9-tri-O-acetyl-2,3,5-trideoxy-2,3-didehydro-β-D-galacto-2,8-nondiulopyranosid)onate 、 原甲酸三甲酯 在 硫酸 作用下， 反应 48.0h， 以38%的产率得到methyl (5-acetamido-4,7-di-O-acetyl-2,3,5-trideoxy-2,3-didehydro-β-D-galacto-2,8-nondiulopyranosid)onate 8,8-dimethylacetal
  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