methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-3-acetamido-2-[4-[[(2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxymethyl]triazol-1-yl]-5-acetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate | 1287768-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-3-acetamido-2-[4-[[(2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxymethyl]triazol-1-yl]-5-acetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate
• CAS: 1287768-49-3
• 化学式: C₈₂H₈₇N₁₁O₃₁
• 分子量: 1722.65
• InChiKey: HPAQTZQBROCUAN-BJEVEKLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  124
• 可旋转键数：
  43
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  507
• 氢给体数：
  3
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-3-acetamido-2-[4-[[(2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxymethyl]triazol-1-yl]-5-acetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate 在 HLiO₂ 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z
• 作为产物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-azidooxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate 、 methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-prop-2-ynoxyoxane-2-carboxylate 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-3-acetamido-2-[4-[[(2S,3S,4S,5R,6R)-6-[4-[[(2R,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-2-(acetyloxymethyl)-6-phenylmethoxyoxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-2-methoxycarbonyloxan-3-yl]oxymethyl]triazol-1-yl]-5-acetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate
  参考文献：
  名称：

  Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

  摘要：

  Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted azido-glucuronic acid and propargyluted N-acetyl glucosamine and N-acetyl galactosamine derivative, respectively. The resulting suitably substituted tetrasaccharide analogues can be easily converted into azide and alkyne unit for further synthesis of higher oligosaccharide analogues.

  DOI：

  10.1021/jo200076z