phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside | 1287768-28-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-7-benzoyloxy-2-(4-methoxyphenyl)-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 1287768-28-8
• 化学式: C₃₄H₃₀O₈S
• 分子量: 598.673
• InChiKey: RMBCZQCUNKSPAU-INFHBARSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 叠氮基三甲基硅烷 、 二氯苯酚溴酯 、 四氯化锡 、 caesium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.5h， 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：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 吡啶 、 camphor-10-sulfonic acid 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside
  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.