(+/-)-trans-2-(α-hydroxy-3,4-methylenedioxybenzyl)-3-(3,4-dimethoxy-α-hydroxybenzyl)butanolide

• 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: (+/-)-trans-2-(α-hydroxy-3,4-methylenedioxybenzyl)-3-(3,4-dimethoxy-α-hydroxybenzyl)butanolide
• 英文别名: (3S,4R)-3-[(S)-1,3-benzodioxol-5-yl(hydroxy)methyl]-4-[(S)-(3,4-dimethoxyphenyl)-hydroxymethyl]oxolan-2-one
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: NFUTVEUXIDZXGJ-YGHPHNMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile 在 sodium tetrahydroborate 、 Catharanthus roseus cell culture in B-5 medium 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 122.0h， 生成 (+/-)-trans-2-(α-hydroxy-3,4-methylenedioxybenzyl)-3-(3,4-dimethoxy-α-hydroxybenzyl)butanolide
  参考文献：
  名称：

  Enzyme-catalyzed Dediastereomerization of Dibenzylbutanolides by Plant Cell Cultures

  摘要：

  We have been developed a novel biocatalytic dediastereornerization method, i. e., reactions allowing the transformation of two diastereorners into one diastereomer in quantitative yield. When a mixture of two diastereomers (4R*-5) and (4S*-5) (1:1 ratio) was subjected to Catharanthus roseus cells in B5 medium, dediastereornerization took place to give a single diastereomer (4R*-5) in 80 % chemical yield with 100 % diastereomeric excess and 0 % enantiomeric excess.

  DOI：

  10.3987/com-01-s(k)22

文献信息

• Dediastereomerization of Dibenzylbutanolides by Plant Cell Cultures
  作者：Masumi Takemoto、Yuki Matsuoka、Kiyoshi Tanaka、James Peter Kutney

  DOI：10.3987/com-06-s(w)18

  日期：——

  When a mixture of two diastereomers (4R*-3) and (4S*-3) was subjected to plant cell cultures, hydrolysis of acetate and dediastereornerization took place to give a single diastereomer (4R*-1) with 100% diastereomeric excess and 0% enantiomeric excess.
• Biocatalytic dediastereomerization of dibenzylbutanolides by plant cell cultures
  作者：Masumi Takemoto、Yuki Matsuoka、Kazuo Achiwa、James Peter Kutney

  DOI：10.1016/s0040-4039(99)02100-0

  日期：2000.1

  A biocatalytic dediastereomerization method, i.e. reactions allowing the transformation of two diastereomers into one diastereomer in quantitative yield, has been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.