(3R,4R)-3-Hydroxy-4-(3-methoxybenzyl)tetrahydrofuran | 147200-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3R,4R)-3-Hydroxy-4-(3-methoxybenzyl)tetrahydrofuran
• 英文别名: (3R,4R)-4-[(3-methoxyphenyl)methyl]oxolan-3-ol
• CAS: 147200-47-3
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: PDEYTOKYTZBWEJ-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-Hydroxy-4-(3-methoxybenzyl)tetrahydrofuran 在 正丁基锂 、 甲基锂 作用下， 反应 22.0h， 生成 (3S,4S)-4-(3-Methoxybenzyl)-3-<(3-methoxyphenyl)(phenylthio)methyl>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
• 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 、 硫酸 、 氢气 、 硼酸 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 15.5h， 生成 (3R,4R)-3-Hydroxy-4-(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

• 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%.