Acetic acid (2R,3S)-3-acetoxymethyl-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-butyl ester | 215377-58-5

• 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: Acetic acid (2R,3S)-3-acetoxymethyl-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-butyl ester
• CAS: 215377-58-5
• 化学式: C₂₆H₃₄O₈
• 分子量: 474.551
• InChiKey: NHXZFSUHPPWVEE-SZPZYZBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S)-3-acetoxymethyl-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-butyl ester 在 Candida antarctica lipase 、 乙醇 作用下， 以 异丙醚 、 苯 为溶剂， 反应 23.0h， 以80%的产率得到Acetic acid (2S,3R)-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-3-hydroxymethyl-butyl ester
  参考文献：
  名称：

  A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone

  摘要：

  The stereoselective acetylation of meso-2,3-bis(3,4-dimethoxybenzyl)butanediol by vinyl acetate in the presence of Candida antarctica lipase in benzene gave the corresponding (+)-(2S,3R) monoester (ee greater than or equal to 98%). Transesterification of meso-2,3-bis(3,4-dimethoxybenzyl)butyl diacetate, in the presence of the same enzyme, by ethanol in benzene/isopropyl ether gave the corresponding (-)-(2R,3S) monoester (ee greater than or equal to 98%). Both enantiomers of the known cis-2,3-bis(3,4-dimethoxybenzyl)butyrolactone were synthesized from these monoesters. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00299-7
• 作为产物：
  描述：

  meso-2,3-diveratryl-succinic acid dimethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 Acetic acid (2R,3S)-3-acetoxymethyl-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-butyl ester
  参考文献：
  名称：

  A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone

  摘要：

  The stereoselective acetylation of meso-2,3-bis(3,4-dimethoxybenzyl)butanediol by vinyl acetate in the presence of Candida antarctica lipase in benzene gave the corresponding (+)-(2S,3R) monoester (ee greater than or equal to 98%). Transesterification of meso-2,3-bis(3,4-dimethoxybenzyl)butyl diacetate, in the presence of the same enzyme, by ethanol in benzene/isopropyl ether gave the corresponding (-)-(2R,3S) monoester (ee greater than or equal to 98%). Both enantiomers of the known cis-2,3-bis(3,4-dimethoxybenzyl)butyrolactone were synthesized from these monoesters. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0957-4166(98)00299-7