ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside | 887478-24-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-3,4-diacetyloxy-5-azido-6-[(2R,3S,4S,5R,6R)-5-azido-2-ethylsulfanyl-6-methyl-4-phenylmethoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 887478-24-2
• 化学式: C₂₇H₃₆N₆O₁₀S
• 分子量: 636.683
• InChiKey: WGNGPQSDSIUHJW-FVZVWMFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 、 2-(trimethylsilyl)ethyl 2-O-benzyl-α-L-fucopyranolyl-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以57%的产率得到2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->3)-2-O-benzyl-α-L-fucopyranolyl-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic Escherichia coli O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside

  摘要：

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.

  DOI：

  10.1080/07328300500495878
• 作为产物：
  描述：

  (3aS,4R,6R,7R,7aS)-7-Azido-2,2-dibutyl-4-ethylsulfanyl-6-methyl-tetrahydro-1,3,5-trioxa-2-stanna-indene 在 4 A molecular sieve 、 四丁基溴化铵 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.5h， 生成 ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Tetrasaccharide Repeating Unit of the O‐Antigen from Enterohemorrhagic Escherichia coli O157 in the form of its 2‐(trimethylsilyl)ethyl Glycoside

  摘要：

  Two alpha-linked disaccharide derivatives, ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl-(1 -> 2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-alpha-D-mannopyranoside (10) and 2-(trimethylsilyl)ethyl 3-O-acetyl-4-O-benzoyl-2-O-benzyl-alpha-L-fucopyranosyl-(1 -> 4)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-beta-D-glucopyranoside (16), were prepared from appropriate monosaccharide synthons. The disaccharide 16 was deacetylated and debenzoylated to afford the acceptor 17, which was allowed to react with the donor 10 to afford a tetrasaccharide derivative 18. This tetrasaccharide was transformed in three steps into 21, the desired repeating unit of the antigen from enterohemorrhagic E. coli type O157.

  DOI：

  10.1080/07328300500495878