15260-83-0

Basic information

• Product Name: 5,5-dimethylthiazolidine-4-carboxylic acid
• Synonyms: 5,5-dimethylthiazolidine-4-carboxylic acid;5,5-Dimethyl-4-thiazolidinecarboxylic acid;(RS)-4-Carboxy-5,5-dimethylthiazolidine
• CAS NO: 15260-83-0
• Molecular Formula: C₆H₁₁NO₂S
• Molecular Weight: 161.22204
• EINECS: 239-305-0
• Mol File: 15260-83-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 200-201 °C (decomp)
• Boiling Point: 317.3°Cat760mmHg
• Flash Point: 145.7°C
• Appearance: /
• Density: 1.195g/cm³
• Vapor Pressure: 8.23E-05mmHg at 25°C
• Refractive Index: 1.516
• PKA: 2.11±0.40(Predicted)
• CAS DataBase Reference: 5,5-dimethylthiazolidine-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethylthiazolidine-4-carboxylic acid(15260-83-0)
• EPA Substance Registry System: 5,5-dimethylthiazolidine-4-carboxylic acid(15260-83-0)

Safety Data

• Hazardous Substances Data: 15260-83-0(Hazardous Substances Data)

Usage

General Description

5,5-dimethylthiazolidine-4-carboxylic acid is a chemical compound with the molecular formula C6H11NO2S. It is a derivative of thiazolidine and is often used as a precursor in the synthesis of pharmaceuticals. 5,5-dimethylthiazolidine-4-carboxylic acid is a stable, white crystalline solid and is slightly soluble in water. 5,5-dimethylthiazolidine-4-carboxylic acid is known for its ability to act as a protectant against oxidative stress and has potential antioxidant properties. It has also been researched for its potential role in the treatment of various metabolic disorders, such as diabetes and obesity. Overall, this chemical compound has potential applications in both the pharmaceutical and nutraceutical industries due to its unique molecular structure and biological properties.

InChI:InChI=1/C6H11NO2S/c1-6(2)4(5(8)9)7-3-10-6/h4,7H,3H2,1-2H3,(H,8,9)

Upstream product

• 50-00-0 formaldehyd 
• 52-66-4 DL-Penicillamin 
• 13206-49-0 5,5-dimethyl-thiazolidine-4-carbonitrile 
• 59-53-0 NAP 
• 101115-49-5 N-acetyl-S-benzyl-DL-penicillamine 
• 15679-22-8 5,5-dimethyl-2,5-dihydro-1,3-thiazole 
• 64-17-5 ethanol 

Downstream Products

• 857960-22-6 3-benzoyl-5,5-dimethylthiazolidine-4-carboxylic acid 
• 943250-59-7 5,5-dimethyl-N-nitrosothiazolidine-4-carboxylic acid 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 287408-72-4 (4S)-3-{[4-(2-butynyloxy)phenyl]sulfonyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 

Relevant articles and documents

'Higher-order' azomethine ylides in the synthesis of functionalized pyrroles and 5-oxo-5H-pyrrolizines

Azafulvenium methides generated by the thermal extrusion of SO2 from 1-methyl- and 1,1-dimethyl-1H,3H-pyrrolo[1,2-c]thiazole-2,2-dioxides undergo [1,8]H sigmatropic shifts to give vinylpyrroles. Flash vacuum pyrolysis of the C-vinylpyrroles affords 5-oxo-5H-pyrrolizines or C-allyl-1H-pyrroles.

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.

Biologically oriented organic sulfur chemistry. 19. Synthesis and properties of 2-amino-5-mercapto-5-methylhexanoic acid, a bishomologue of penicillamine. Use of boron trifluoride etherate for catalyzing Markownikoff addition of a thiol to an olefin

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