(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide | 111194-09-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide
• 英文别名: 3-(4-benzyloxy-3-methoxybenzyl)-2-[(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide；(3S,4R)-3-[(S)-hydroxy-(3-methoxy-4-phenylmethoxyphenyl)methyl]-4-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one
• CAS: 111194-09-3
• 化学式: C₃₄H₃₄O₇
• 分子量: 554.64
• InChiKey: MODNSZVIEDYUTM-ZIINUWHCSA-N

物化性质

• 沸点：
  737.9±60.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-4-butanolide 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 22.0h， 以63%的产率得到(αR,βR)-α,β-双(4-羟基-3-甲氧苯基)丁内酯
  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 、 (R)-(+)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 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 2.25h， 以88%的产率得到(2S,3R)-3-(4-benzyloxy-3-methoxybenzyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)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

文献信息

• Syntheses of all eight stereoisomers of conidendrin
  作者：Hinako Shirakata、Hisashi Nishiwaki、Satoshi Yamauchi

  DOI：10.1080/09168451.2020.1777081

  日期：2020.10.2

  All eight stereoisomers of conidendrin were synthesized from (1 R,2 S,3 S)-1-(4-benzyloxy-3-methoxyphenyl)-3-(4-benzyloxy-3-methoxybenzyl)-2- hydroxymethyl-1,4-butanediol ((+)-4) and its enantiomer with high optical purity. The configurations at 4-positions of the conidendrin stereoisomers were constructed by intramolecular Friedel-Crafts reaction of protected 4. After conversion to tetrahydronaphthalene

  从（1 R，2  S，3  S）-1-（4-苄氧基-3-甲氧基苯基）-3-（4-苄氧基-3-甲氧基苄基）-2-羟甲基-1,4合成分生孢子蛋白的所有八个立体异构体 -具有高光学纯度的-丁二醇（（+）- 4）及其对映异构体。通过被保护的4的分子内Friedel-Crafts反应，构建了分生孢子蛋白立体异构体4位的构型。转化为四氢萘中间体7a后，将四氢萘结构7a的2-位和3-位分别转化为（+）-α-分枝烯苷（3a）的3a位和9a位。通过2a或3位7a的差向异构过程，获得了其他非对映异构体。所有对映体也由（-）- 4合成。
• Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans
  作者：Satoshi Yamauchi、Yoshimasa Hayashi、Yuki Nakashima、Takuya Kirikihira、Kazuki Yamada、Toshiya Masuda

  DOI：10.1021/np050089s

  日期：2005.10.1

  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.