19041-15-7

Basic information

• Product Name: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE
• Synonyms: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE;(S)-GAMMA-VALEROLACTONE;(5S)-4-Hydroxypentanoic acid lactone;(5S)-5-Methyloxolan-2-one;(S)-5-Methyl-2-oxotetrahydrofuran;(S)-Dihydro-5-methyl-2(3H)-furanone;(S)-γ-Methyl-γ-butyrolactone;(S)-γ-Valerolactone
• CAS NO: 19041-15-7
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.12
• Mol File: 19041-15-7.mol
• Article Data: 66

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• BRN: 3536337
• CAS DataBase Reference: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(19041-15-7)
• EPA Substance Registry System: (S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE(19041-15-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 19041-15-7(Hazardous Substances Data)

Usage

Description

(S)-GAMMA-METHYL-GAMMA-BUTYROLACTONE, a chiral compound belonging to the class of lactones, is a cyclic ester with a non-superimposable mirror image. It has been researched for its potential as a precursor in the synthesis of pharmaceuticals and other organic compounds, as well as for its pharmacological effects, such as acting as a prodrug for GHB or modulating GABA receptor function. Its role in various chemical reactions and processes makes it a compound of interest in the fields of organic synthesis and drug discovery.

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

• 14872-53-8 S-γ-methyl-(R/S)-α-carbethoxy-γ-butyrolactone 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 118574-86-0 4-benzoyloxy-5(S)-methyl-2(5H)-furanone 
• 108-59-8 malonic acid dimethyl ester 
• 16088-62-3 (S)-Propylene oxide 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 64-17-5 ethanol 
• 2854-10-6 levulinic acid t-butyl ester 
• 624-45-3 levulinic acid methyl ester 
• 1219498-06-2 (S)-2-[(S)-4-hydroxypentanamide]-3-phenyl-N-[(R)-1-phenylethyl]propanamide 
• 6089-09-4 4-pentynoic acid 
• 55077-16-2 phenyl levulinate 
• 10229-10-4 pent-3-yn-1-ol 
• 126252-14-0 (+/-)-γ-hydroxy-γ-methylbutyric acid methylester 

Downstream Products

• 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 
• 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 
• 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 
• 119326-52-2 (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 
• 108675-63-4 geodiamolide A 
• 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 
• 112775-67-4 (3RS,5S)-3-phenylseleno-5-methyldihydro-2(3H)-furanone 

Relevant articles and documents

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.

Asymmetric Reduction of Chlorinated 4-Oxopentanoates with Bakers' Yeast. Synthesis of Optically Active γ-Butyrolactones and Useful Chiral Building Blocks

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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.

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.

Stereoselective Reactions of Ester Enolates with Epoxides

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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 hydrogenation of unsaturated carbonyl compounds catalyzed by BINAP-Ru(II) complexes. Enantioselective synthesis of γ-butyrolactones and cyclopentanones

Asymmetric hydrogenation of 2- and 4-alkylidene-γ-butyrolactones and 2-alkylidenecyclopentanones catalyzed by BINAP-Ru(II) complexes affords the corresponding γ-butyrolactones and cyclopentanones in 94-98% ee. Hydrogenation of (E)- and (Z)-2-propylidene-γ-butyrolactone catalyzed by the same catalyst gave the products with the same absolute configuration and in almost equal enantioselectivities, which shows that olefin geometry does not affect the stereochemistry and enantioselectivity.

Iridium-Catalyzed Asymmetric Hydrogenation of ?- A nd ?-Ketoacids for Enantioselective Synthesis of ?- A nd ?-Lactones

A highly efficient asymmetric hydrogenation of ?- A nd ?-ketoacids was developed by using a chiral spiro iridium catalyst (S)-1a, affording the optically active ?- A nd ?-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Chiron approach towards optically pure γ-valerolactone from alanine

A concise synthesis of both enantiomers of γ-valerolactone has been developed from commercially available Alanine. The key steps in the synthesis of these γ-Lactones are DIBAL-H reduction of ester (9) followed by in situ Wittig reaction with EtO2CCH = PPh3 ylide (13) (Z/E = 1: 3.5) and one pot lactonization triggered by deprotection of O-TBS ether (14).