(S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester

• 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: (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester
• 英文别名: propan-2-yl (2S)-5-oxooxolane-2-carboxylate
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: BHANLYCWXLHWHW-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester 在 titanium(IV) isopropylate 、 溴丁基-镁 、 magnesium 、 溶剂黄146 、 1,2-二溴乙烷 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 苯 为溶剂， 反应 5.5h， 生成 2-[{(7S)-5,5-dimethyl-4,6-dioxaspiro[2.4]hept-7-yl}methyl]-1-[4-methylpent-4-enyl]cyclopropyl methanesulfonate
  参考文献：
  名称：

  环氧丙烷中间体的强制应用合成埃坡霉素D

  摘要：

  在连续的环丙烷化的中间阶段进行六次应用的埃博霉素D的全合成-打开或裂解三元环。这些转变是为偶联目标分子中的片段C 7 -C 12和C 13 -C 21而开发的新的立体选择性方法的基础。

  DOI：

  10.1134/s1070428011110029
• 作为产物：
  描述：

  (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester 生成 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid i-propyl ester
  参考文献：
  名称：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

  摘要：

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00286-4

文献信息

• Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates
  作者：Sara Drioli、Patrizia Nitti、Giuliana Pitacco、Laura Tossut、Ennio Valentin

  DOI：10.1016/s0957-4166(99)00286-4

  日期：1999.7

  Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic gamma-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of epothilone D with the forced application of oxycyclopropane intermediates
  作者：A. L. Hurski、O. G. Kulinkovich

  DOI：10.1134/s1070428011110029

  日期：2011.11

  The total synthesis of epothilone D with six-fold application in the intermediate stages of successive cyclopropanation — opening or cleavage of the three-membered ring was performed. These transformations underlie the new stereoselective method developed for coupling fragments C7–C12 and C13–C21 in the target molecule.

  在连续的环丙烷化的中间阶段进行六次应用的埃博霉素D的全合成-打开或裂解三元环。这些转变是为偶联目标分子中的片段C 7 -C 12和C 13 -C 21而开发的新的立体选择性方法的基础。