methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranosyl-(1→4)-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside | 1428556-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranosyl-(1→4)-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside
• 英文别名: (2S,3R,4R,5S,6S)-3-azido-2-[(2S,3S,4R,5R,6S)-5-azido-2-(iodomethyl)-6-methoxy-4-phenylmethoxyoxan-3-yl]oxy-6-(iodomethyl)-5-methoxy-4-phenylmethoxyoxane
• CAS: 1428556-09-5
• 化学式: C₂₈H₃₄I₂N₆O₇
• 分子量: 820.423
• InChiKey: ZTNQLYKVHFRANU-QLJCWTAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranosyl-(1→4)-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 、 乙酸酐 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以62%的产率得到methyl 2-acetamido-2,6-dideoxy-4-O-methyl-α-D-glucopyranosyl-(1→4)-2-acetamido-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the Upstream Terminal Disaccharide of theO-Antigenic Polysaccharide ofVibrio choleraeO37

  摘要：

  The terminal disaccharide of the O-antigenic polysaccharide of Vibrio cholerae O37, 4-O-methyl-alpha-D-QuiNAc-(1 -> 4)-alpha-D-QuiNAc, was synthesized as methyl glycoside involving glycosylation between glycosyl donor ethyl 2-azido-3-O-benzyl-2,6-dideoxy-4-O-methyl-6-iodo-1-thio-alpha-D-glucopyranoside and glycosyl acceptor methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-alpha-D-glucopyranoside. Dehalogenation, global deprotection, and reduction of the azide to amine were effected in one step by catalytic hydrogenation. It was followed by selective N-acetylation to give the desired deprotected disaccharide.

  DOI：

  10.1080/07328303.2012.722738
• 作为产物：
  描述：

  methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 咪唑 、 N-碘代丁二酰亚胺 、 碘 、 溶剂黄146 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranosyl-(1→4)-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the Upstream Terminal Disaccharide of theO-Antigenic Polysaccharide ofVibrio choleraeO37

  摘要：

  The terminal disaccharide of the O-antigenic polysaccharide of Vibrio cholerae O37, 4-O-methyl-alpha-D-QuiNAc-(1 -> 4)-alpha-D-QuiNAc, was synthesized as methyl glycoside involving glycosylation between glycosyl donor ethyl 2-azido-3-O-benzyl-2,6-dideoxy-4-O-methyl-6-iodo-1-thio-alpha-D-glucopyranoside and glycosyl acceptor methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-alpha-D-glucopyranoside. Dehalogenation, global deprotection, and reduction of the azide to amine were effected in one step by catalytic hydrogenation. It was followed by selective N-acetylation to give the desired deprotected disaccharide.

  DOI：

  10.1080/07328303.2012.722738