methyl 2-azido-3-O-benzyl-2-deoxy-4-O-methyl-6-O-tosyl-α-D-glucopyranoside | 1428556-03-9

• 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-deoxy-4-O-methyl-6-O-tosyl-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-azido-3,6-dimethoxy-4-phenylmethoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1428556-03-9
• 化学式: C₂₂H₂₇N₃O₇S
• 分子量: 477.538
• InChiKey: RSXALJBADDNPDX-LMYCIYFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3-O-benzyl-2-deoxy-4-O-methyl-6-O-tosyl-α-D-glucopyranoside 、 乙酸酐 在 硫酸 、 溶剂黄146 作用下， 反应 2.0h， 以71.429%的产率得到
  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-2-deoxy-4-O-methyl-6-O-trityl-α-D-glucopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 24.0h， 生成 methyl 2-azido-3-O-benzyl-2-deoxy-4-O-methyl-6-O-tosyl-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