methyl (methyl 4,5-diacetamido-7,8,9-tri-O-acetyl-3-bromo-3,4,5-trideoxy-α-D-glycero-D-talo-nonulopyranosid)onate | 173096-86-1

• 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 (methyl 4,5-diacetamido-7,8,9-tri-O-acetyl-3-bromo-3,4,5-trideoxy-α-D-glycero-D-talo-nonulopyranosid)onate
• CAS: 173096-86-1
• 化学式: C₂₁H₃₁BrN₂O₁₂
• 分子量: 583.387
• InChiKey: DLZXOTSNFVUKGJ-KDQGOHMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (methyl 4,5-diacetamido-7,8,9-tri-O-acetyl-3-bromo-3,4,5-trideoxy-α-D-glycero-D-talo-nonulopyranosid)onate 在 sodium hydroxide 、 偶氮二异丁腈 、 Dowex 50 NH₄⁺ 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 ammonium (methyl 4,5-diacetamido-3,4,5-trideoxy-α-D-glycero-D-talo-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of methyl 4-acetamido-N-acetyl-4-deoxy-α- and β-4-epi-neuraminic acids

  摘要：

  Methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3,4,5-tetradeoxy-D-glycero-D-talo- nonulopyranosonate with N-bromosuccinimide in methanol gave methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-alpha-D-ralo-nonulopyranosid) and methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-beta-D-glycero-D-talo-nonulopyranosid)onate, which on reductive acetylation with H-2/Pd-C in acetic anhydride-ethyl acetate yielded the corresponding 4-acetamido analogues. Debromination with Bu(3)SnH/AIBN in toluene, followed by hydrolysis, gave methyl 4-acetamido-N-acetyl-4-deoxy-alpha-and beta-4-epi-neuraminic acids.

  DOI：

  10.1016/0008-6215(95)00191-u
• 作为产物：
  描述：

  methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3-didehydro-2,3,4,5-tetradeoxy-D-glycero-D-talo-2-nonulopyranosidonate 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、344.73 kPa 条件下， 反应 18.0h， 生成 methyl (methyl 4,5-diacetamido-7,8,9-tri-O-acetyl-3-bromo-3,4,5-trideoxy-α-D-glycero-D-talo-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of methyl 4-acetamido-N-acetyl-4-deoxy-α- and β-4-epi-neuraminic acids

  摘要：

  Methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-2,3,4,5-tetradeoxy-D-glycero-D-talo- nonulopyranosonate with N-bromosuccinimide in methanol gave methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-alpha-D-ralo-nonulopyranosid) and methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3-bromo-3,4,5-trideoxy-beta-D-glycero-D-talo-nonulopyranosid)onate, which on reductive acetylation with H-2/Pd-C in acetic anhydride-ethyl acetate yielded the corresponding 4-acetamido analogues. Debromination with Bu(3)SnH/AIBN in toluene, followed by hydrolysis, gave methyl 4-acetamido-N-acetyl-4-deoxy-alpha-and beta-4-epi-neuraminic acids.

  DOI：

  10.1016/0008-6215(95)00191-u