benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1287768-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• 英文别名: N-[(2S,4aR,6R,7R,8R,8aR)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 1287768-37-9
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: NXGXFAKJUWEFEC-YGBDOONVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 barium(II) hydroxide 、 barium(II) oxide 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 11.0h， 生成 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-(methoxymethoxy)oxane-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
• 作为产物：
  描述：

  benzyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  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.