19041-15-7

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE is used as a precursor in the synthesis of pharmaceuticals and other organic compounds due to its unique chemical properties and potential for creating new and effective medications.
Used in Organic Synthesis:
(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE is used as a key intermediate in various organic synthesis processes, contributing to the development of novel chemical compounds and materials.
Used in Drug Discovery:
(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE is used as a compound of interest in drug discovery, with potential pharmacological effects such as acting as a prodrug for GHB or modulating GABA receptor function, which could lead to the development of new therapeutic agents.
Used in Chemical Reactions and Processes:
(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE is utilized in various chemical reactions and processes, playing a crucial role in the advancement of organic synthesis techniques and the creation of innovative chemical products.

Upstream product

• 58879-35-9 (5R)-(iodomethyl)-γ-butyrolactone 
• 126252-14-0 (+/-)-γ-hydroxy-γ-methylbutyric acid methylester 
• 14872-53-8 S-γ-methyl-(R/S)-α-carbethoxy-γ-butyrolactone 
• 111043-99-3 (R)-(-)-γ-hydroxy-γ-methylbutyric acid methylester 
• 112789-84-1 (+)-(S)-ethyl 4-hydroxypentanoate 
• 136118-31-5 (S)-(+)-4-hydroxypentanenitrile 
• 120294-54-4 tert-butyl (4S)-4-hydroxypentanoate 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 624-45-3 levulinic acid methyl ester 
• 693783-93-6 propyl 4-hydroxy-5-phenylselanylpentanoate 
• 3128-06-1 5-ketohexanoic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 99631-16-0 ethyl (S)-4-hydroxypentanoate 
• 136801-92-8 [(S)-5-Methyl-dihydro-furan-(2E)-ylidene]-acetic acid methyl ester 

Downstream Products

• 112775-67-4 (3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone 
• 108675-63-4 geodiamolide A 
• 119326-52-2 (S)-2-((S)-3-(4-Hydroxy-3-iodo-phenyl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-hydroxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid 
• 119326-51-1 (S)-2-((S)-3-(4-Hydroxy-3-iodo-phenyl)-2-{[(S)-2-((E)-(2S,6R,8S)-8-hydroxy-2,4,6-trimethyl-non-4-enoylamino)-propionyl]-methyl-amino}-propionylamino)-propionic acid methyl ester 
• 119326-50-0 (S)-2-[(S)-2-({(S)-2-[(E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoylamino]-propionyl}-methyl-amino)-3-(4-hydroxy-3-iodo-phenyl)-propionylamino]-propionic acid methyl ester 
• 126187-54-0 (1S,2S)-2-methyl-(trans-2-phenylethenyl)cyclopropane 
• 126187-55-1 (1R,2S)-2-methyl-(trans-2-phenylethenyl)cyclopropane 
• 58927-89-2 S-6-phenyl-5-hexen-2-ol 
• 126110-35-8 R-trans-5-chloro-1-phenyl-1-hexene 
• 92998-79-3 (S)-(-)-α-(2-chlorobenzylidene)-γ-methyl-γ-butyrolactone 
• 681218-99-5 (S)-6-(triisopropylsiloxy)hept-2-en-1-yl para-toluenesulfonate 
• 18545-25-0 S-(-)-γ-methyl-(R/S)-γ-butyrolactol 

Relevant academic research and scientific papers

Direct asymmetric reduction of levulinic acid to gamma-valerolactone: synthesis of a chiral platform molecule

Levulinic acid was directly converted to optically active (S)-gamma-valerolactone, a proposed biomass-based chiral platform molecule. By using a SEGPHOS ligand-modified ruthenium catalyst in methanol as a co-solvent, eventually, 100% chemoselectivity, and 82% enantioselectivity were achieved. The effect of the catalyst composition and reaction parameters on the activity and selectivity was investigated in detail. The conversion of a "real" biomass derived levulinic acid to optically active GVL without decreasing the enantioselectivity was also demonstrated.

Dynamic kinetic resolution of γ-hydroxy acid derivatives

Enzymatic resolution and dynamic kinetic resolution of γ-hydroxy acid derivatives 1 have been investigated. Efficient kinetic resolution was obtained using Pseudomonas cepacia lipase in toluene (E value ～400). The combination of enzymatic kinetic resoluti

Facile Synthesis of Optically-Active Γ-Valerolactone from Levulinic Acid and Its Esters Using a Heterogeneous Enantio-Selective Catalyst

Abstract: Optically-active γ-valerolactone was synthesized by the enantio-selective hydrogenations of levulinic acid and its esters. A tartaric acid-NaBr-modified nickel catalyst produced the optically-active γ-valerolactone with a 60% enantiomeric excess (ee), almost quantitative conversion and chemoselectivity. The synthesis of the optically-active γ-valerolactone using the enantio-selective heterogeneous catalyst would be promising for the large-scale industrial production from levulinic acid and its esters, which can be obtained by the acid-catalyzed dehydration of cellulosic fraction of biomass. Graphical Abstract: [Figure not available: see fulltext.].

The role of protic solvent in asymmetric hydrogenation of methyl levulinate in the presence of a ruthenium-containing catalyst

A comparative study of asymmetric hydrogenation and deuteration of methyl levulinate catalyzed by the RuII-(S)-BINAP-HCl system (BINAP is 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) in MeOH and MeOD was carried out. The results obtained suggest an important role of the protic solvent in the formation of catalytically active ruthenium complexes.

Allergenic α-Methylene-γ-butyrolactones. Stereospecific Syntheses of (+)- and (-)-γ-Methyl-α-methylene-γ-butyrolactones. A Study of the Specificity of (+) and (-) Enantiomers in Inducing Allergic Contact Dermatitis

The enantiomers of γ-methyl-α-methylene-γ-butyrolactone have been prepared stereospecifically from (R)- and (S)-glutamic acid.Three groups of guinea pigs have been sensitized (Feund complete adjuvant technique) to the (+)-isomer, the (-)-isomer, and the (+/-)-mixture.The animals have been tested with each of the enantiomers and with a mixture of the compounds.Only the (-) enantiomer showed some specificity: guinea pigs sensitized to this enantiomer react weakly to the other compound; in turn, animals sensitized to the (+) enantiomer react similarly to both antipodes.Interestingly, reaction to the (+/-) mixture in each group of guinea pigs was the sum of skin responses to the individual enantiomer.These results should be contrasted with sensitization to (+)- and (-)-frullanolides, sesquiterpene lactones for which strong stereospecificity was observed.

Access to lactone building blocks via horse liver alcohol dehydrogenase-catalyzed oxidative lactonization

The oxidative lactonization of 1,4-, 1,5-, and 1,6-diols using horse liver alcohol dehydrogenase (HLADH) is reported. Molecular oxygen was used as terminal electron acceptor by utilization of the laccase-mediator concept to regenerate the oxidized nicotinamide cofactor and producing water as sole byproduct. Spontaneous hydrolysis of the lactone products was identified as a major limiting factor toward preparative application of the system, which can be alleviated by using a two liquid phase approach to extracting the product into an organic solvent.

Enantioselective, electrocatalytic lactonization of methyl-substituted diols on a TEMPO-modified graphite felt electrode in the presence of (-)-sparteine

A TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxyl)-modified graphite felt electrode afforded enantioselective, electrocatalytic lactonized products of (S)-(-)-3,4,5,6-tetrahydro-4-melhyl-2-pyranone, (S)-(-)-4,5-dihydro-4-methyl-2(3H)-furanone and (S)-(-)-4,5-dihydro-5-methyl-2(3H)-furanone from 3-methylpentane-1,5-diol, (S)-(-)-2-methylbutane-1,4-diol and racemic pentane-1,4-diol, respectively, in enantiomeric excess more than 95%, in the presence of (-)-sparteine in acetonitrile. The current efficiency and isolated yield of former two lactones were more than 90%.

Synthesis of (5S)-5-methylfuran-2(5H)-one and its dihydro derivative

(5S)-5-Methylfuran-2(5H)-one and (5S)-5-methyltetrahydrofuran-2-one were synthesized starting from L-lactic acid ethyl ester.

Kinetic resolution and chemoenzymatic dynamic kinetic resolution of functionalized γ-hydroxy amides

(Chemical Equation Presented) An efficient kinetic resolution of racemic γ-hydroxy amides 1 was performed via Pseudomas cepacia lipase (PS-C)-catalyzed transesterification. The enzyme PS-C tolerates both variation in the chain length and different functionalities giving good to high enantioselectivity (E values of up to >250). The combination of enzymatic kinetic resolution with a ruthenium-catalyzed racemization led to a dynamic kinetic resolution. The use of 2,4-dimethyl-3-pentanol as a hydrogen source to suppress ketone formation in the dynamic kinetic resolution yields the corresponding acetates in good yield and good to high enantioselectivity (ee's up to 98%). The synthetic utility of this procedure was illustrated by the practical synthesis of the versatile intermediate γ-lactone (R)-5-methyltetrahydrofuran-2-one.

Asymmetric cyclization of unsaturated alcohols and carboxylic acids with camphor-based selenium electrophiles

The diastereoselective cyclization of a series of unsaturated alcohols and carboxylic acids was achieved with chiral camphor-based selenenyl chlorides, of which the spirooxazolidinone 3c proved the most effective.