methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-prop-2-ynoxyoxane-2-carboxylate | 1287768-41-5

• 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,3S,4R,5R,6R)-5-acetamido-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-prop-2-ynoxyoxane-2-carboxylate
• CAS: 1287768-41-5
• 化学式: C₅₆H₅₆N₄O₁₄
• 分子量: 1009.08
• InChiKey: TWYRYTYHABFVSL-RTXOETQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  74
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  203
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-4-acetyloxy-2-(acetyloxymethyl)-6-azidooxan-3-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate 、 methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-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， 以87%的产率得到C₉₂H₉₅N₁₁O₂₉
  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：

  β-D-葡萄糖胺五乙酸酯 在 三乙基硅烷 、 copper(l) iodide 、 三氟甲磺酸 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 barium(II) hydroxide 、 barium(II) oxide 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.5h， 生成 methyl (2S,3S,4S,5R,6R)-6-[4-[[(2R,3S,4R,5R,6R)-5-acetamido-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxymethyl]triazol-1-yl]-4,5-dibenzoyloxy-3-prop-2-ynoxyoxane-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

文献信息

• Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks
  作者：Smritilekha Bera、Robert J. Linhardt

  DOI：10.1021/jo200076z

  日期：2011.5.6

  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.