1-O-acetyl-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranose | 1428556-05-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-α-D-glucopyranose
• 英文别名: [(2R,3R,4R,5S,6S)-3-azido-6-(iodomethyl)-5-methoxy-4-phenylmethoxyoxan-2-yl] acetate
• CAS: 1428556-05-1
• 化学式: C₁₆H₂₀IN₃O₅
• 分子量: 461.256
• InChiKey: CJRGKAZZFVDKHM-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-methyl-6-O-tosyl-D-glucopyranose 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87.5%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