33019-03-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE is used as a building block for the synthesis of pharmaceuticals and other organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, facilitating the development of new molecules with potential therapeutic applications.
Used in Organic Chemistry Research:
(R)-(-)-GAMMA-ETHOXYCARBONYL-GAMMA-BUTYROLACTONE is used as a versatile intermediate in organic chemistry research for exploring various organic transformations. Its ability to engage in multiple chemical reactions makes it an essential component in the synthesis of complex organic molecules and the advancement of organic chemistry knowledge.

InChI:InChI=1/C7H10O4/c1-2-10-7(9)5-3-4-6(8)11-5/h5H,2-4H2,1H3/t5-/m1/s1

Upstream product

• 1126-51-8 (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 69556-79-2 (–)-(R)-diethyl 2-hydroxyglutarate 
• 328-50-7 α-ketoglutaric acid 
• 69134-53-8 (+/-)-diethyl 2-hydroxypentandioate 
• 5965-53-7 diethyl 2-ketoglutarate 
• 13095-48-2 L-hydroxyglutaric acid 
• 141-78-6 ethyl acetate 
• 21461-85-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester 
• 64-17-5 ethanol 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 

Downstream Products

• 147058-39-7 1-(2,3-dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine 
• 208173-52-8 (R)-5-Hydroxy-tetrahydro-furan-2-carboxylic acid ethyl ester 
• 1309671-47-3 C₅₁H₅₅N₂O₅P 
• 1309671-53-1 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5,5-di(pyren-1-yl)pentan-2-ol 
• 1309671-44-0 (S)-1-[bis(4-methoxyphenyl)phenylmethoxy]-5-(pyren-1-yl)pentan-2-ol 
• 1309671-51-9 (S)-1-(benzyloxy)-5,5-(dipyren-1-yl)pentan-2-ol 
• 1309671-49-5 (S)-5-(benzyloxy)-1,1-(dipyren-1-yl)pentan-1,4-diol 
• 1309671-42-8 (S)-1-(benzyloxy)-5-(pyren-1-yl)pentan-2-ol 
• 1309671-55-3 C₆₇H₆₃N₂O₅P 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 155768-47-1 -Ethyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 

Relevant academic research and scientific papers

Ring-opened 4-hydroxy-δ-valerolactone subunit as a key structural fragment of polyesters that degrade without acid formation

Random copolymers of ?-caprolactone with O-benzyl-protected 4-hydroxy- or 2,4-dihydroxy-δ-valerolactone after hydrogenation form γ-hydroxy functionalized polyesters that degrade via the cyclization to γ-butyrolactone fragments without carboxylic acid formation.

Pyrene intercalating nucleic acids with a carbon linker

We have synthesized a carbon linker analogue of INA (oligonucleotides containing insertions of 1-O-(1-pyrenylmethyl)glycerol). Thermal stability studies showed an increase in melting temperature in favor of the carbon linker analogue. We also synthesized a carbon linker analogue with two pyrenes geminally attached. Fluorescence studies of this intercalating nucleic acid with the pyrene moieties inserted as a bulge showed formation of an excimer band. When a mismatch was introduced at the site of the intercalator, an excimer band was formed for the destabilized duplexes whereas an exciplex band was observed when the stability of the duplex was retained. Copyright Taylor and Francis Group, LLC.

Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid

An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.

Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo- 2-furancarboxylic acids and esters

Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned γ- lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd.

Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts

The first direct asymmetric synthesis of chiral alkyl 5- oxotetrahydrofuran-2-carboxylates (up to 96% ee), which are important building blocks in the synthesis of natural products by heterogeneous cinchona-modified Pt-catalyzed hydrogenation of α-ketoglutaric acid esters and subsequent cyclization of hydroxy esters is described.

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

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-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.

Diastereocontrol in Glycosylation Reactions: Synthesis of β-D and β-L Dideocytidine Analogues

Expeditious and diastereoselective total syntheses of the antiviral agents, β-L-ddC, β-L-5FddC and β-D-5FddC have been achieved in four steps from commercially available R-(-)-5-oxo-2-tetrahydrofurancarboxylic and its 2S isomer respectively.

Anti-HIV and Anti-HBV Activities of L-2',3'-dideoxynucleoside Analogues: ddC, 5FddC, 5-Aza ddC and ddG

The antiviral activities of the L-enantiomers of the title nucleoside analogues were determined in vitro. β-L-ddC and β-L-5FddC showed significant activity against the replication of HIV-1 and HBV, whereas β-L-5-aza ddC and β-L-ddG were devoid of such activities.

SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID

L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.