(3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran | 868128-05-6

• 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: (3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran
• CAS: 868128-05-6
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: IZWOMFBOKNVPLR-BHZGVWCHSA-N

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到(8R,8'S)-3,3'-methoxy-9,9'-epoxylignane-4,4'-diol
  参考文献：
  名称：

  First Discovery of Insecticidal Activity of 9,9′-Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure–Activity Relationship

  摘要：

  The insecticidal activity of (-)-(8R,8'R)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8'R)-stereoisomer. In the course of research into structure activity relationships involving 30 newly synthesized (8R,8'R)-derivatives, 5-fold higher activity (ED50 = 0.91 nmol/fly) was observed for (-)-(8R,8'R)-3,3',4-trimethoicy-9,9'-epoxylignan-4'-ol (21) than for the naturally occurring compound (1). The activity of I was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4.

  DOI：

  10.1021/jf400300n
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以0.79 g的产率得到(3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)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