ethyl (3S,4R)-(-)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate | 869594-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: ethyl (3S,4R)-(-)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate
• CAS: 869594-37-6
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: DGOQRTXHTGOCJQ-PHDIDXHHSA-N

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4R)-(-)-4-methyl-5-oxo-tetrahydrofuran-3-carboxylate 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (3R,4S)-(-)-methyl-4-(2-methyl-1,3-dithiolan-2-yl)-2(3H)-dihydrofuranone
  参考文献：
  名称：

  A combined experimental and computational strategy in the assignment of absolute configurations of 4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acids and their esters

  摘要：

  Enantiopure cis- and trans-4-methylparaconic acids and their alkyl esters were synthesized by a procedure involving the kinetic enzymatic resolution of diastereomeric lactonic esters. Thus, ethyl cis- and trans-4-methyl-5-oxo-tetrahydrofuran-3-carboxylates were isolated, at high conversion values, with 99% ee from the hydrolyses with HLAP and alpha-CT, respectively. The corresponding enantiopure cis- and trans-lactonic acids were also obtained. The absolute configurations of the products were assigned by chemical correlation, by analysis of their circular dichroism spectra and by electronic structure calculations. All three methodologies lead to the same assignment for the species considered, another example of successful interplay between experiment and theory. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.08.018