80963-80-0

Basic information

• Product Name: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate
• Synonyms: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate
• CAS NO: 80963-80-0
• Molecular Formula: C₅H₇NO₂S₂
• Molecular Weight: 177.24
• Mol File: 80963-80-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate(80963-80-0)
• EPA Substance Registry System: (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate(80963-80-0)

Safety Data

• Hazardous Substances Data: 80963-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(-)-methyl (R)-2-thioxothiazolidine-4-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique molecular structure and properties, contributing to the development of new drugs and treatments.
Used in Antimicrobial Applications:
In the field of microbiology, (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate is used as an antimicrobial agent, leveraging its ability to inhibit the growth of harmful microorganisms, thereby offering potential in the creation of new antimicrobial therapies and products.
Used in Antioxidant Formulations:
(-)-methyl (R)-2-thioxothiazolidine-4-carboxylate is used as an antioxidant in various formulations, including cosmetics, food products, and pharmaceuticals, to protect against oxidative damage and extend shelf life or maintain product integrity.
Used in Organic Chemistry Research:
In the realm of organic chemistry, (-)-methyl (R)-2-thioxothiazolidine-4-carboxylate is used as a research compound to explore new chemical reactions, mechanisms, and the synthesis of complex organic molecules, furthering scientific understanding and innovation in the field.

Upstream product

• 67-56-1 methanol 
• 98169-56-3 (4R)-2-sulfanylidene-1,3-thiazolidine-4-carboxylic acid 
• 81912-43-8 (R)-3-Hexadecanoyl-2-thioxo-thiazolidine-4-carboxylic acid methyl ester 
• 24461-61-8 phenylglycine methyl ester 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 

Downstream Products

• 81925-64-6 methyl 3-benzoyl-2-thioxothiazolidine-4-carboxylate 
• 129921-96-6 3-(3(R)-(3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(R)-oxazolidinyl)-3-hydroxy-2(R)-isopropyl-1-oxopropyl)-4(S)-(methoxycarbonyl)-1,3-thiazolidine-2-thione 
• 129921-96-6 (4S,5S)-4-Cyclohexylmethyl-5-[(1R,2R)-1-hydroxy-2-((R)-4-methoxycarbonyl-2-thioxo-thiazolidine-3-carbonyl)-3-methyl-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 108082-37-7 (R)-3-((2R,3S)-3-Hydroxy-2-phenylsulfanyl-hexanoyl)-2-thioxo-thiazolidine-4-carboxylic acid methyl ester 
• 108082-35-5 (R)-3-[(R)-2-((R)-Hydroxy-phenyl-methyl)-butyryl]-2-thioxo-thiazolidine-4-carboxylic acid methyl ester 
• 108082-33-3 (R)-3-((2R,3R)-3-Hydroxy-2-methyl-3-phenyl-propionyl)-2-thioxo-thiazolidine-4-carboxylic acid methyl ester 
• 97919-91-0 C₂₀H₂₆N₂O₆S₄ 
• 97919-89-6 C₂₀H₂₄N₂O₆S₄ 
• 108082-31-1 N-<(phenoxythio)acetoxy>-4(R)-(methoxycarbonyl)-1,3-thiazolidine-2-thione 

Relevant articles and documents

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.

Novel Chiral Bifunctional L-Thiazoline-Thiourea Derivatives: Design and Application in Enantioselective Michael Reactions

Several novel chiral bifunctional L-thiazoline-thiourea derivatives were easily synthesized from commercially available L-cysteine in high yield. These catalysts were subsequently applied to the enantioselective Michael addition of acetylacetone to β-nitr

Novel chiral bifunctional L-thiazoline-amide derivatives: Design and application in the direct enantioselective aldol reactions

Several novel chiral bifunctional l-thiazoline-amide derivatives were simply synthesized from commercially available l-cysteine and l-proline in high yield. These catalysts were subsequently applied to the direct enantioselective aldol reactions of variou

A versatile synthesis of various substituted taurines from vicinal amino alcohols and aziridines

Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid, oxidation of the thiazolidine-2-thione intermediates generated from, vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines.

The Use of Cysteine- and Serine-Derived Thiazolidinethiones and Oxazolidinethiones as Efficient Chiral Auxiliaries an Aldol Condensations

Cysteine-derived thiazolidinethiones and serine-derived oxazolidinethiones serve as efficient chiral auxiliaries in boron- and tin-mediated aldol condensations.The condensations with a variety of simple aldehydes produced the expected erythro products in high chemical and optical yields.Additional advantages of these chiral auxiliaries were the ease of removal by methanolysis or hydroxaminolysis and their practical recyclability.

Highly Selective Nonenzymatic Chiral Induction into 3-Methylglutaric Acid and cis-4-Cyclohexen-1,2-ylenebis(acetic acid) Utilizing a Functional Five-Membered Heterocycle 4(R)-MCTT

Diamide 8, prepared by treatment of 3-methylglutaric acid (1) with 4(R)-MCTT (5) in the presence of DCC in pyridine, was subjected to aminolysis with 1 equiv of piperidine in CH2Cl2 at -30 deg C to give a mixture of diastereomers 9a and 10a in a 88:12 rat

SYNTHESIS OF 1,3-THIAZOLIDINE-2-THIONE AND (4R)-METHOXYCARBONYL-1,3-THIAZOLIDINE-2-THIONE USING N,N'-THIOCARBONYLDIIMIDAZOLE

1,3-Thiazolidine-2-thiones are synthesized from β-aminothiols and N,N'-thiocarbonyldiimidazole in good yields.

A NEW CHIRAL RECOGNITION IN AMINOLYSIS OF 3-ACYL-4(R)-METHOXYCARBONYL-1,3-THIAZOLIDINE-2-THIONE WITH RACEMIC AMINES

A chiral recognition was observed in aminolysis of 3-acyl-4(R)-methoxycarbonyl-1,3-thiazolidine-2-thione 1 by racemic amine 2 to give an optically active amide (S-excess) and amine (R-excess).