(2aS,3R,8aR)-5-benzyloxy-3-(4-benzyloxy-3-methoxyphenyl)-6-methoxy-2,2a,8,8a-tetrahydronaphthalene[2,3-c]tetrahydrofuran | 868128-06-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (2aS,3R,8aR)-5-benzyloxy-3-(4-benzyloxy-3-methoxyphenyl)-6-methoxy-2,2a,8,8a-tetrahydronaphthalene[2,3-c]tetrahydrofuran
• CAS: 868128-06-7
• 化学式: C₃₄H₃₄O₅
• 分子量: 522.641
• InChiKey: KBYOQLMZFRKOTM-LTGROYGMSA-N

反应信息

• 作为反应物：
  描述：

  (2aS,3R,8aR)-5-benzyloxy-3-(4-benzyloxy-3-methoxyphenyl)-6-methoxy-2,2a,8,8a-tetrahydronaphthalene[2,3-c]tetrahydrofuran 在 palladium on activated charcoal 氢气 作用下， 反应 16.0h， 以100%的产率得到(2aS,3S,8aR)-5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2,2a,8,8a-tetrahydronaphthalene[2,3-c]tetrahydrofuran
  参考文献：
  名称：

  Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans

  摘要：

  It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding gamma-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.

  DOI：

  10.1021/np050089s
• 作为产物：
  描述：

  (3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran 反应 48.0h， 以100%的产率得到(2aS,3R,8aR)-5-benzyloxy-3-(4-benzyloxy-3-methoxyphenyl)-6-methoxy-2,2a,8,8a-tetrahydronaphthalene[2,3-c]tetrahydrofuran
  参考文献：
  名称：

  Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans

  摘要：

  It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding gamma-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.

  DOI：

  10.1021/np050089s