methyl (5R)-2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-5-O-methoxalyl-β-D-xylo-hexofuranoside | 1449769-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (5R)-2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-5-O-methoxalyl-β-D-xylo-hexofuranoside
• CAS: 1449769-66-7
• 化学式: C₂₈H₃₆NO₁₂P
• 分子量: 609.567
• InChiKey: ORXXJRIGSVIAJY-DPAWKBHVSA-N

反应信息

• 作为产物：
  描述：

  甲基戊酰氯 、 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-β-D-xylo-hexofuranoside 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 methyl (5R)-2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-5-O-methoxalyl-β-D-xylo-hexofuranoside 、 methyl (5S)-2-acetamido-3,6-di-O-benzyl-2-deoxy-5-C-dimethoxyphosphoryl-5-O-methoxalyl-β-D-xylo-hexofuranoside
  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