53684-30-3

Basic information

• Product Name: ethyl cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate
• CAS NO: 53684-30-3
• Molecular Weight: 234.252
• Mol File: 53684-30-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate(53684-30-3)
• EPA Substance Registry System: ethyl cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate(53684-30-3)

Safety Data

• Hazardous Substances Data: 53684-30-3(Hazardous Substances Data)

Upstream product

• 53684-30-3 ethyl cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 
• 10539-50-1 diethyl 2-benzoylsuccinate 
• 97149-57-0 2,2-Diethoxy-cyclopropanecarboxylic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 56579-54-5 Ethyl 2,2-dimethoxycyclopropane-1-carboxylate 

Downstream Products

• 1084874-78-1 ethyl (2R,3R)-(-)-trans-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 
• 1084874-76-9 ethyl (2S,3S)-(+)-trans-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 
• 1084874-73-6 ethyl (2R,3S)-(+)-cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 
• 1084874-77-0 ethyl (2S,3R)-(-)-cis-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 
• 53684-30-3 ethyl trans-5-oxo-2-phenyl-tetrahydrofuran-3-carboxylate 

Relevant articles and documents

Chemoenzymatic and yeast-catalysed synthesis of diastereomeric ethyl γ-phenyl and γ-(n-pyridyl)paraconates

The synthesis of γ-phenyl and γ-(n-pyridyl)paraconates was accomplished by chemical reduction of their respective ketodiester precursors followed by cyclisation of the resulting hydroxy diester intermediates. The cis- and trans-lactones thus obtained were separated and separately subjected to enzymatic hydrolysis with HLAP. The cis-lactonic esters had enantiomeric excesses ranging from 94% to 99%, while for the trans-isomers the ee's ranged from 80% to 93%. The same ketodiester precursors were subjected to reduction with a series of yeasts. The absolute configuration of trans-(-)-2-pyridyl paraconic acid was assigned by means of X-ray analysis of its hydrobromide salt, while the absolute configurations of the other lactones were determined via analysis of their respective CD curves.