ethyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-1-thio-α-D-glucopyranoside | 1428556-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-1-thio-α-D-glucopyranoside
• CAS: 1428556-07-3
• 化学式: C₁₆H₂₂IN₃O₃S
• 分子量: 463.339
• InChiKey: UIQPGVVZECAMCM-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-α-D-glucopyranoside 、 ethyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-1-thio-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.75h， 生成 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：

  1-O-acetyl-2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-D-glucopyranose 、 乙硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到ethyl 2-azido-3-O-benzyl-2,6-dideoxy-6-iodo-4-O-methyl-1-thio-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