(3S,4S,5S)-5-((S)-acetoxy(3,4-dimethoxyphenyl)methyl)-4-(2-bromo-4,5-dimethoxyphenyl)tetrahydrofuran-3-yl acetate | 1537880-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S,5S)-5-((S)-acetoxy(3,4-dimethoxyphenyl)methyl)-4-(2-bromo-4,5-dimethoxyphenyl)tetrahydrofuran-3-yl acetate
• CAS: 1537880-90-2
• 化学式: C₂₅H₂₉BrO₉
• 分子量: 553.404
• InChiKey: QMYCWTZYSNLVTP-ROHNOIKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-5-((S)-acetoxy(3,4-dimethoxyphenyl)methyl)-4-(2-bromo-4,5-dimethoxyphenyl)tetrahydrofuran-3-yl acetate 在 palladium diacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 邻二甲苯 为溶剂， 反应 24.0h， 以46%的产率得到(4bS,5S,7aS,8S,12bR)-2,3,11,12-tetramethoxy-5,6,7a,8-tetrahydro-4bH-dibenzo[3,4:5,6]cyclohepta[1,2-b]furan-5,8-diyl diacetate
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055
• 作为产物：
  描述：

  hydroxymetasequirin A tetramethyl ether diacetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以79%的产率得到(3S,4S,5S)-5-((S)-acetoxy(3,4-dimethoxyphenyl)methyl)-4-(2-bromo-4,5-dimethoxyphenyl)tetrahydrofuran-3-yl acetate
  参考文献：
  名称：

  An Organocatalytic Asymmetric Allylic Alkylation Allows Enantioselective Total Synthesis of Hydroxymetasequirin-A and Metasequirin-B Tetramethyl Ether Diacetates

  摘要：

  The first highly stereoselective organocatalytic intermolecular allylic alkylation of allylic alcohols with 1,3-dicarbonyls has been developed to allow the first enantioselective total synthesis of hydroxymetasequirin-A and metasequirin-B tetramethyl ether diacetates.

  DOI：

  10.1021/ol4037055