(2R,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-1,4-butannediol | 868127-92-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-1,4-butannediol
• CAS: 868127-92-8
• 化学式: C₅₂H₇₈O₈Si₂
• 分子量: 887.358
• InChiKey: BBTHTEOEWJZEDI-BBRNPXLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.25
• 重原子数：
  62.0
• 可旋转键数：
  25.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  95.84
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-1,4-butannediol 在 吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以52%的产率得到(3R,4R)-3-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]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：

  (2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以65%的产率得到(2R,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-1,4-butannediol
  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

文献信息

• Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7′-Oxodihydroguaiaretic Acid
  作者：Satoshi YAMAUCHI、Toshiya MASUDA、Takuya SUGAHARA、Yuya KAWAGUCHI、Maya OHUCHI、Tatsushi SOMEYA、Jun AKIYAMA、Shiori TOMINAGA、Manami YAMAWAKI、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.80461

  日期：2008.11.23

  The antioxidant activity of butane-type lignans was evaluated. Secoisolariciresinol (SECO) and dihydroguaiaretic acid (DGA) showed higher radical scavenging activity than that of 7,7′-dioxodihydroguaiaretic acid (ODGA). SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity.

  对丁烷类木酚素的抗氧化活性进行了评估。与 7,7′-二氧二氢愈创木脂酸（ODGA）相比，仲异月桂醇（SECO）和二氢愈创木脂酸（DGA）具有更高的自由基清除活性。SECO 和 DGA 可抑制不饱和脂肪酸的氧化。DGA 的两种对映体也是脂氧合酶抑制剂，但 SECO 的两种对映体都不能抑制脂氧合酶的活性。