2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-> 4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose | 743427-24-9

• 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: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-> 4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose
• 英文别名: Glc2Ac3Ac4Ac6Ac(a1-4)keto-Fru1Ac3Ac5Ac6Br；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4S)-2,4,6-triacetyloxy-1-bromo-5-oxohexan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 743427-24-9
• 化学式: C₂₆H₃₅BrO₁₇
• 分子量: 699.458
• InChiKey: VOYSDGQJRCYLOU-MJTKXXFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  44
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  220
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-> 4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose 在 palladium dihydroxide sodium azide 、 氢气 、 sodium methylate 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 268.0h， 生成 α-D-glucopyranosyl-(1-> 3)-N-(5-cyanopentyl)-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Golgi endomannosidase inhibitor, α-d-glucopyranosyl-(1→3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives

  摘要：

  Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1-->4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30degreesC, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.015
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-> 4)-1,3,5-tri-O-acetyl-D-fructopyranose 在 triphenylphosphine dibromide 1:1 addition complex 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以85%的产率得到2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1-> 4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose
  参考文献：
  名称：

  Golgi endomannosidase inhibitor, α-d-glucopyranosyl-(1→3)-1-deoxymannojirimycin: a five-step synthesis from maltulose and examples of N-modified derivatives

  摘要：

  Acid-catalysed O-acetylation of D-maltulose furnished the corresponding per-O-acetylated fructopyranose derivative that, after in situ deprotection at O-2 by reaction with triphenylphosphane dibromide, gave open-chain 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1-->4)-1,3,5-tri-O-acetyl-6-bromo-6-deoxy-D-fructose. Standard deprotection employing sodium methoxide in methanol at -30degreesC, followed by treatment of the resulting free 6-bromodeoxymaltulose with sodium azide in N,N-dimethylformamide, allowed access to 6-azidodeoxymaltulose. Hydrogenation over Pearlman's catalyst, accompanied by intramolecular reductive amination, yielded the desired title compound. This route allows access to preparative quantities and to a range of novel analogues with improved biostability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.015