p-methoxyphenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 1609244-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• CAS: 1609244-63-4
• 化学式: C₉₂H₁₀₂N₆O₂₅
• 分子量: 1691.85
• InChiKey: VKKRCIVQLAAQIO-RYNJJITKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.71
• 重原子数：
  123.0
• 可旋转键数：
  36.0
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  351.79
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 三乙基硅烷 、 palladium 10% on activated carbon 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of a pentasaccharide repeating unit of the O-antigen of enteroadherent Escherichia coli O154 strain

  摘要：

  A straightforward linear synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigenic polysaccharide of enteroadherent Escherichia coli O154 strain. Newly developed glycosylation conditions using glycosyl trichloroacetimidate derivatives as glycosyl donors and nitrosyl tetrafluoroborate as the glycosylation activator have been used in all of the glycosylation reactions throughout the synthetic scheme. The stereochemical outcomes of the glycosylations were excellent and the yields were very good. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.007
• 作为产物：
  描述：

  p-methoxyphenyl (2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-L-galactopyranoside 、 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl) trichloroacetimidate 在 nitrosonium tetrafluoroborate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.67h， 以71%的产率得到p-methoxyphenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a pentasaccharide repeating unit of the O-antigen of enteroadherent Escherichia coli O154 strain

  摘要：

  A straightforward linear synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigenic polysaccharide of enteroadherent Escherichia coli O154 strain. Newly developed glycosylation conditions using glycosyl trichloroacetimidate derivatives as glycosyl donors and nitrosyl tetrafluoroborate as the glycosylation activator have been used in all of the glycosylation reactions throughout the synthetic scheme. The stereochemical outcomes of the glycosylations were excellent and the yields were very good. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.007