(2S,3aS,8aR)-4-Benzyloxy-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-carboxylic acid methyl ester | 156693-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: (2S,3aS,8aR)-4-Benzyloxy-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3aR,8bS)-6-methoxy-8-phenylmethoxy-1,2,3a,8b-tetrahydrofuro[2,3-b][1]benzofuran-2-carboxylate
• CAS: 156693-65-1
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: YNXRKKYZBLXQPA-VHFSOBRXSA-N

物化性质

• 沸点：
  477.7±45.0 °C(predicted)
• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3aS,8aR)-4-Benzyloxy-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-carboxylic acid methyl ester 在 potassium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 48.0h， 生成 (3aS,8aS)-2-Acetoxy-4-(benzyloxy)-6-methoxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran
  参考文献：
  名称：

  Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2

  摘要：

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.

  DOI：

  10.1021/jo00093a008
• 作为产物：
  描述：

  (2S)-4-(Benzyloxy)-2-carboxy-6-hydroxy-2,3,3a,8a-tetrahydrofuro<2,3-b>benzofuran 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以45%的产率得到(2S,3aR,8aS)-4-Benzyloxy-6-methoxy-2,3,3a,8a-tetrahydro-benzo[b]furo[3,2-d]furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the Enantiomeric Furobenzofurans, Late Precursors for the Synthesis of (+)- and (-)-Aflatoxins B1, B2, G1, and G2

  摘要：

  Enantiomeric tetrahydrofuro[2,3-b]benzofurans, representing the ABC tricyclic portion of aflatoxins B-1, B-2, G(1), and G(2), were generated from the oxaza-Cope rearrangement of a suitably functionalized O-aryloxime. The O-aryloxime was, in turn, made from the condensation of an enantiomerically pure aldehyde derived from glutamic acid and a substituted phenoxyamine. High regioselectivity with respect to the A-ring substituents of the ABC tricycle was achieved through the use of electrochemistry. The regioselective electrochemical cleavage of 4,6-bis(tosyloxy)-2-(methoxycarbonyl)-2,3,3a,8a-tetrahydrofuro[2,3-b]benzofuran (22) resulted in a 97/3 mixture of regioisomeric phenols. The regiochemical assignments of the resulting phenols were determined by 2D NOESY NMR. The enantiomeric ratio of the final product was determined to be 96/4 by NMR analysis of diastereomers resulting from the coupling of 31a to (+)- and (+/-)-phenethylamine.

  DOI：

  10.1021/jo00093a008