(3R,4R)-3,4-Bis(3-methoxybenzyl)tetrahydrofuran

• 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,4R)-3,4-Bis(3-methoxybenzyl)tetrahydrofuran
• 英文别名: (3R,4R)-3,4-bis[(3-methoxyphenyl)methyl]oxolane
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: XOMXFRGFFGQGKM-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-methoxybenzaldehyde oxime 在 palladium on activated charcoal 、 W-2 Ra-Ni 吡啶 、 N-氯代丁二酰亚胺 、 正丁基锂 、 乙酸乙烯酯 、 硫酸 、 甲基锂 、 氢气 、 硼酸 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 70.5h， 生成 (3R,4R)-3,4-Bis(3-methoxybenzyl)tetrahydrofuran
  参考文献：
  名称：

  Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions

  摘要：

  Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S(N)2 displacement of tosylates 15 and 18 by alpha-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)-tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%.

  DOI：

  10.1021/jo00060a037

文献信息

• Synthetic butanolide and tetrahydrofuran lignans with platelet activating factor antagonist activity
  作者：SA Coran、M Bambagiotti-Alberti、F Melani、V Giannellini、FF Vincieri、N Mulinacci、R Sala、E Moriggi

  DOI：10.1016/0223-5234(91)90200-7

  日期：1991.9

  Several butanolide and tetrahydrofuran lignans were synthesized to be comparatively tested as platelet activating factor (PAF) antagonists. In particular, the influence of the tetrahydrofurans ether oxygen as compared with the gamma-lactone system of butanolides was evaluated, showing that the two classes of compounds were practically bioisosters. Molecular modelling and semi-empirical calculation were used to rationalize the collected data.
• Enantiocontrolled synthesis of burseran, brassilignan, dehydroxycubebin, and other tetrahydrofuran lignans in both enantiomeric forms. Application of intermolecular nitrile oxide cycloadditions and lipase-mediated kinetic resolutions
  作者：Janet A. Gaboury、Mukund P. Sibi

  DOI：10.1021/jo00060a037

  日期：1993.4

  Several natural and unnatural tetrahydrofuran lignans have been synthesized by a convergent approach. Our methodology utilizes a nitrile oxide cycloaddition to dihydrofuran 8 and an enzymatic resolution of alcohols 11 by lipase PS. The lipase-mediated kinetic resolution of alcohols 11 furnished both enantiomers of the lignan precursors 12 and 14 in high optical purity (>99% ee). This is followed by a S(N)2 displacement of tosylates 15 and 18 by alpha-lithiobenzyl phenyl sulfides. In this manner, both enantiomers of 3,4-dibenzyltetrahydrofuran (17a, 20a), 3,4-bis(3-methoxybenzyl)-tetrahydrofuran (17b, 20b), brassilignan (17c, 20c), dehydroxycubebin (17d, 20d), and burseran (17e, 20e) were synthesized in overall yields of 6-16%.