N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-6-O-acetyl-2,4-di-Obenzyl-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl-(1→4)-2,3,6-tri-Obenzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside | 1429920-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-6-O-acetyl-2,4-di-Obenzyl-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl-(1→4)-2,3,6-tri-Obenzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3S,4S,5R,6S)-6-[(2R,3R,4R,5S,6R)-2-[5-[benzyl(phenylmethoxycarbonyl)amino]pentoxy]-5-phenylmethoxy-6-(phenylmethoxymethyl)-3-[(2,2,2-trichloroacetyl)amino]oxan-4-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-(naphthalen-2-ylmethoxy)-3,5-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 1429920-37-5
• 化学式: C₁₀₂H₁₀₇Cl₃N₂O₁₉
• 分子量: 1771.33
• InChiKey: HTUNUYSQQFVGMG-QISMUFQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  126
• 可旋转键数：
  46
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  214
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-6-O-acetyl-2,4-di-Obenzyl-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl-(1→4)-2,3,6-tri-Obenzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  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：

  ethyl 6-O-acetyl-2,4-di-O-benzyl-3-O-(2-naphthylmethyl)-1-thio-β-D-glucopyranoside 、 N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl-(1→3)-4,6-di-O-benzyl-2-trichloroacetamido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.25h， 以97%的产率得到N-(benzyl)benzyloxycarbonyl-5-aminopentanyl-6-O-acetyl-2,4-di-Obenzyl-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl-(1→4)-2,3,6-tri-Obenzyl-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