58310-00-2

Basic information

• Product Name: (2R)-diethyl-2-ethyl-1,4-succinate
• CAS NO: 58310-00-2
• Molecular Weight: 174.197
• Mol File: 58310-00-2.mol

Chemical Properties

• CAS DataBase Reference: (2R)-diethyl-2-ethyl-1,4-succinate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-diethyl-2-ethyl-1,4-succinate(58310-00-2)
• EPA Substance Registry System: (2R)-diethyl-2-ethyl-1,4-succinate(58310-00-2)

Safety Data

• Hazardous Substances Data: 58310-00-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 687-28-5 S-(-)-2-ethylsuccinic acid 
• 29737-65-3 dimethyl trans-3-methylenecyclopropane-1,2-dicarboxylate 
• 636-48-6 monoethylsuccinic acid 
• 3952-66-7 methyl 2-oxobutanoate 
• 84565-22-0 dimethyl 2-ethylfumarate 

Downstream Products

• 74650-57-0 R-(-)-N-benzyl-3-ethylpyrrolidine 

Relevant articles and documents

Steric effects on the stereochemistry of old yellow enzyme-mediated reductions of unsaturated diesters: Flipping of the substrate within the enzyme active site induced by structural modifications

The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2- substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. Methyl 2-substituted fumarates were reduced to enantiomerically enriched methyl (S)-2-substituted succinates, whereas the (Z)-stereoisomers were left unreacted by enereductases. Labelling experiments were performed to investigate the mechanism of these bioreductions and explain their stereochemical outcome.