4-O-benzoyl-2-O-benzyl-3,6-dideoxy-L-xylo-hexopyranosyl-N-phenyl trifluoroacetimidate | 1429920-26-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-O-benzoyl-2-O-benzyl-3,6-dideoxy-L-xylo-hexopyranosyl-N-phenyl trifluoroacetimidate
• 英文别名: [(2S,3S,5S,6S)-2-methyl-5-phenylmethoxy-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxan-3-yl] benzoate
• CAS: 1429920-26-2
• 化学式: C₂₈H₂₆F₃NO₅
• 分子量: 513.513
• InChiKey: UVQQROLARRAZCZ-ZWDKEWGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-2,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside 、 4-O-benzoyl-2-O-benzyl-3,6-dideoxy-L-xylo-hexopyranosyl-N-phenyl trifluoroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以63%的产率得到N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-3,6-dideoxy-4-O-benzoyl-2-O-benzyl-α-L-xylo-hexopyranosyl-(1→3)-[3,6-dideoxy-4-O-benzoyl-2-O-benzyl-α-L-xylo-hexopyranosyl-(1→6)]-2,4-di-O-benzyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Total Synthesis of theEscherichia coliO111O-Specific Polysaccharide Repeating Unit

  摘要：

  AbstractThe first total synthesis of the O‐antigen pentasaccharide repeating unit from Gram‐negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis‐glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non‐carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.

  DOI：

  10.1002/chem.201204394
• 作为产物：
  描述：

  (2S,3S,5S)-5-(benzyloxy)-6-hydroxy-2-(naphthalen-2-ylmethoxy)hexan-3-yl benzoate 在 吡啶 、 caesium carbonate 、 戴斯-马丁氧化剂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-O-benzoyl-2-O-benzyl-3,6-dideoxy-L-xylo-hexopyranosyl-N-phenyl trifluoroacetimidate
  参考文献：
  名称：

  Total Synthesis of theEscherichia coliO111O-Specific Polysaccharide Repeating Unit

  摘要：

  AbstractThe first total synthesis of the O‐antigen pentasaccharide repeating unit from Gram‐negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis‐glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non‐carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.

  DOI：

  10.1002/chem.201204394

文献信息

• Total Synthesis of the<i>Escherichia coli</i>O111<i>O</i>-Specific Polysaccharide Repeating Unit
  作者：Oliviana Calin、Steffen Eller、Heung Sik Hahm、Peter H. Seeberger

  DOI：10.1002/chem.201204394

  日期：2013.3.18

  AbstractThe first total synthesis of the O‐antigen pentasaccharide repeating unit from Gram‐negative bacteria Escherichia coli O111 was achieved starting from four monosaccharide building blocks. Key to the synthetic approach was a bis‐glycosylation reaction to combine trisaccharide 10 and colitose 5. The colitose building block (5) was obtained de novo from non‐carbohydrate precursors. The pentasaccharide was equipped at the reducing end with an amino spacer to provide a handle for subsequent conjugation to a carrier protein in anticipation of immunological studies.