2-acetamido-6-O-benzyl-2,5-dideoxy-5-dimethoxyphosphoryl-3,4-O-isopropylidene-D-glucose dimethyl acetal | 1449769-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-acetamido-6-O-benzyl-2,5-dideoxy-5-dimethoxyphosphoryl-3,4-O-isopropylidene-D-glucose dimethyl acetal
• 英文别名: N-[(1R)-1-[(4R,5S)-5-[(1R)-1-[dimethoxy(oxido)phosphaniumyl]-2-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethoxyethyl]acetamide
• CAS: 1449769-58-7
• 化学式: C₂₂H₃₆NO₉P
• 分子量: 489.503
• InChiKey: SFNIAEPHMOGAGK-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-acetamido-6-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-5-O-methoxalyl-3,4-O-isopropylidene-D-xylo-hexose dimethyl acetal 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以60%的产率得到N-[(1R)-1-[(4R,5S)-5-[(1S)-1-[dimethoxy(oxido)phosphaniumyl]-2-phenylmethoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethoxyethyl]acetamide
  参考文献：
  名称：

  Synthesis of 2-Acetamido-2,5-dideoxy-5-phosphoryl-D-glucopyranose Derivatives: New Phospha-sugar Analogs of N-Acetyl-D-glucosamine

  摘要：

  Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-D-glucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5-dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

  DOI：

  10.3987/com-12-s(n)69