(-)-(3R,4R)-3-(3,4-methylenedioxybenzyl)-4-(3,4,5-trimethoxybenzyl)tetrahydrofuran | 73465-36-8

• 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-(3,4-methylenedioxybenzyl)-4-(3,4,5-trimethoxybenzyl)tetrahydrofuran
• 英文别名: (-)-trans-burseran；(-)-Burseran；burseranin；burseran；5-[[(3R,4R)-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl]methyl]-1,3-benzodioxole
• CAS: 73465-36-8
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: VJMJISPSGHVBBU-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4R)-3-(3,4-methylenedioxybenzyl)-4-(3,4,5-trimethoxybenzyl)tetrahydrofuran 生成 5-[[(3S,4S)-4-[(2-chloro-3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl]methyl]-1,3-benzodioxole
  参考文献：
  名称：

  REHNBERG, NICOLA;MAGNUSSON, GORAN, J. ORG. CHEM., 55,(1990) N4, C. 4340-4349

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(3,4,5-trimethoxybenzylidene)dihydrofuran-2(3H)-one 在 palladium on activated charcoal 吡啶 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酰氯 作用下， 反应 20.0h， 生成 (-)-(3R,4R)-3-(3,4-methylenedioxybenzyl)-4-(3,4,5-trimethoxybenzyl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective reactions. X. Total synthesis of optically pure antitumor lignan, burseran.

  摘要：

  以明确的方式立体选择性地合成了光学纯的反式和顺式-burseran (4, 10)。它们在气相色谱上的行为比较表明天然存在的抗肿瘤木酚素，burseran，是反式异构体。

  DOI：

  10.1248/cpb.33.4333

文献信息

• New platelet activating factor antagonists, named "the phomactins", their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0371762A2

  公开（公告）日：1990-06-06

  A series of new compounds, called "the phomactins" (I and II) is provided and may be isolated from the culture broth of fungi of the genus Phoma, especially Phoma sp. SANK 11486 (No. FERM BP-2598). These compounds are platelet activating factor antagonists and may be used for the treatment of disorders for which known such agents may also be used.

  本研究提供了一系列新化合物，称为 "噬菌体蛋白"（I 和 II），可从噬菌体属真菌，特别是噬菌体 sp. SANK 11486（编号 FERM BP-2598）的培养液中分离出来。这些化合物是血小板活化因子拮抗剂，可用于治疗已知此类药物也可用于治疗的疾病。
• Method of preparing (S)-gamma-hydroxymethyl-alpha, beta-butenolide
  申请人：Japan Tobacco Inc.

  公开号：EP0411403A1

  公开（公告）日：1991-02-06

  A method of preparing (S)-γ-hydroxymethyl-­α,β-butenolide includes the step of oxidizing a levoglucosenone with a peracid in an organic solvent. Peracetic acid, metha-chloroperbenzoic acid or magnesium monoperoxyphthalate hexahydrate can be used as the peracid. According to this method, an (S)-γ-­hydroxymethyl-α,β-butenolide having high optical purity can be easily prepared from a levoglucosenone as a starting material at a high yield.

  制备(S)-γ-羟甲基-α,β-丁烯内酯的方法包括在有机溶剂中用过酸氧化左旋葡烯酮的步骤。过酸可以使用过乙酸、甲氯过苯甲酸或六水单过氧化邻苯二甲酸镁。根据这种方法，可以很容易地以左旋葡糖内酯为起始原料，高产率地制备出具有高光学纯度的 (S)-γ-羟甲基-α,β-丁烯内酯。
• 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%.
• General conjugate-addition method for the synthesis of enantiomerically pure lignans. Total synthesis of (-)- and (+)-burseran, (-)-dehydroxycubebin, (-)-trichostin, (-)-cubebin, (-)-5''-methoxyhinokinin, and (-)-hinokinin
  作者：Nicola Rehnberg、Goeran Magnusson

  DOI：10.1021/jo00301a026

  日期：1990.7
• REHNBERG, NICOLA;MAGNUSSON, GORAN, TETRAHEDRON LETT., 29,(1988) N 29, C. 3599-3602
  作者：REHNBERG, NICOLA、MAGNUSSON, GORAN

  DOI：——

  日期：——