(1R*,2R*,3R*,4S*)-2,3-bis(hydroxymethyl)-1-(3,4-dimethoxyphenyl)-4-<3,4-(methylenedioxy)phenyl>butane-1,4-diol

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (1R*,2R*,3R*,4S*)-2,3-bis(hydroxymethyl)-1-(3,4-dimethoxyphenyl)-4-<3,4-(methylenedioxy)phenyl>butane-1,4-diol
• 英文别名: (1S*,2R*,3R*,4R*)-2,3-Bis(hydroxymethyl)-1-<3,4-(methylenedioxy)phenyl>-4-(3,4-dimethoxyphenyl)butane-1,4-diol；(1S,2R,3R,4R)-1-(1,3-benzodioxol-5-yl)-4-(3,4-dimethoxyphenyl)-2,3-bis(hydroxymethyl)butane-1,4-diol
• 化学式: C₂₁H₂₆O₈
• 分子量: 406.433
• InChiKey: NQKWXDSGKFGHTM-LATRNWQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R*,2R*,3R*,4S*)-2,3-bis(hydroxymethyl)-1-(3,4-dimethoxyphenyl)-4-<3,4-(methylenedioxy)phenyl>butane-1,4-diol 在 吡啶 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到(1S-(1alpha,3aalpha,4beta,6aalpha))-5-(4-(3,4-二甲氧基苯基)四氢-1H,3H-呋喃并(3,4-c)呋喃-1-基)-1,3-苯并二氧戊环
  参考文献：
  名称：

  A novel asymmetric synthesis of axial-equatorial furofuran lignans: A synthesis of (+)-fargesin

  摘要：

  （+）-Fargesin（6）是一个典型的轴-赤道型呋喃木质素类化合物的代表，具有两个不同的芳香基团。它已通过一种高对映选择性的迈克尔加成反应高效合成，其中氰基水合物1与甲基（S）-3-（2,2-二甲基-1,3-二氧杂环戊烷-4-基）顺式-2-丙烯酸酯（2）发生反应。

  DOI：

  10.1016/0040-4039(95)01507-e
• 作为产物：
  描述：

  Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 L-Selectride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 17.67h， 生成 (1R*,2R*,3R*,4S*)-2,3-bis(hydroxymethyl)-1-(3,4-dimethoxyphenyl)-4-<3,4-(methylenedioxy)phenyl>butane-1,4-diol
  参考文献：
  名称：

  Stereocontrolled Syntheses of Diequatorial and Axial-Equatorial Furofuran Lignans

  摘要：

  Methyl piperitol, a representative example of the diequatorial furofuran lignan, was synthesized in a good overall yield based on a highly stereocontrolled conjugate addition-aldol reaction. Fargesin, a representative example of the axial-equatorial furofuran lignans, was also synthesized in a good overall yield based on a new method for inversion of the stereochemistry at C-4 of 5a.

  DOI：

  10.1021/jo00110a016

文献信息

• A novel asymmetric synthesis of axial-equatorial furofuran lignans: A synthesis of (+)-fargesin
  作者：Shin-ichi Yoshida、Takeshi Yamanaka、Tutomu Miyake、Yasunori Moritani、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/0040-4039(95)01507-e

  日期：1995.10

  (+)-Fargesin (6), a representative example of the axial-equatorial furofuran lignans having two different aryl groups, was efficiently synthesized based on a highly diastereoselective Michael addition reaction of the cyanohydrin 1 to methyl (S)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2).

  （+）-Fargesin（6）是一个典型的轴-赤道型呋喃木质素类化合物的代表，具有两个不同的芳香基团。它已通过一种高对映选择性的迈克尔加成反应高效合成，其中氰基水合物1与甲基（S）-3-（2,2-二甲基-1,3-二氧杂环戊烷-4-基）顺式-2-丙烯酸酯（2）发生反应。
• Stereocontrolled Syntheses of Diequatorial and Axial-Equatorial Furofuran Lignans
  作者：Tsuyoshi Ogiku、Shin-ichi Yoshida、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo00110a016

  日期：1995.3

  Methyl piperitol, a representative example of the diequatorial furofuran lignan, was synthesized in a good overall yield based on a highly stereocontrolled conjugate addition-aldol reaction. Fargesin, a representative example of the axial-equatorial furofuran lignans, was also synthesized in a good overall yield based on a new method for inversion of the stereochemistry at C-4 of 5a.
• Asymmetric syntheses of lignans utilizing novel diastereoselective Michael addition of cyanohydrin: Syntheses of (+)-fargesin and (−)-picropodophyllone
  作者：Shin-ichi Yoshida、Takeshi Yamanaka、Tutomu Miyake、Yasunori Moritani、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/s0040-4020(97)00643-1

  日期：1997.7

  The Michael addition reaction of lithium salt of cyanohydrin to (S)- and (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-cis-2-propenoate (2 and 3) proceeded in 93% de in the presence of two equivalents of HMPA at -100 degrees C. This diastereoselectivity could be elucidated by the stereocontrol based on the 1,3-allylic strain. Utilizing this reaction, stereocontrolled syntheses of (+)-fargesin (6) and (-)-picropodophyllone (7) were achieved. (C) 1997 Elsevier Science Ltd.
• First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol
  作者：Shin-ichi Yoshida、Tsuyoshi Ogiku、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo961733y

  日期：1997.3.1

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.