(2R,3S,4S)-2-(4-benzyloxy-3-methoxybenzyl)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-4-butanolide | 868128-04-5

• 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: (2R,3S,4S)-2-(4-benzyloxy-3-methoxybenzyl)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-4-butanolide
• 英文别名: [(2S,3S,4R)-2-(3-methoxy-4-phenylmethoxyphenyl)-4-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-5-oxooxolan-3-yl]methyl 2,2-dimethylpropanoate
• CAS: 868128-04-5
• 化学式: C₃₉H₄₂O₈
• 分子量: 638.758
• InChiKey: UMJHFQLMMWPJNJ-PCJZJSDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-2-(4-benzyloxy-3-methoxybenzyl)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-4-butanolide 在 palladium dihydroxide sodium hydroxide 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 66.0h， 生成 (2R,3S)-2,3-bis(4-hydroxy-3-methoxybenzyl)-4-butanolide
  参考文献：
  名称：

  Antimicrobiological Activity of Lignan: Effect of Benzylic Oxygen and Stereochemistry of 2,3-Dibenzyl-4-butanolide and 3,4-Dibenzyltetrahydrofuran Lignans on Activity

  摘要：

  研究了 2,3-二苄基-4-丁内酯和 3,4-二苄基四氢呋喃木脂素苄基位置的氧化程度对其抗菌活性的影响。2,3-二苄基-4-丁内酯苄基位置的氧化程度最高，其活性最大，而 3,4-二苯甲酰四氢呋喃的抗真菌活性最高。我们还研究了立体化学与活性之间的关系。首次合成了顺式马泰松醇的两种对映体，其中一种顺式马泰松醇具有抗菌活性。

  DOI：

  10.1271/bbb.70168
• 作为产物：
  描述：

  (2S,3S,4S)-4-(4-benzyloxy-3-methoxyphenyl)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-pivaloyloxymethyl-4-butanolide 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到(2R,3S,4S)-2-(4-benzyloxy-3-methoxybenzyl)-4-(4-benzyloxy-3-methoxyphenyl)-3-pivaloyloxymethyl-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