(2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide | 868127-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide
• CAS: 868127-83-7
• 化学式: C₄₃H₅₄O₈Si
• 分子量: 726.982
• InChiKey: RLMAJZIFGJRQPD-SQQATCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.62
• 重原子数：
  52.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide 、 三异丙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以84%的产率得到(2S,3R)-2,3-bis[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide
  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：

  4-苄氧基-3-甲氧基苯甲醛 、 (3R)-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以79%的产率得到(2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide
  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