15260-83-0

Usage

Uses

Used in Pharmaceutical Industry:
5,5-Dimethylthiazolidine-4-carboxylic acid is used as a precursor in the synthesis of pharmaceuticals for its potential role in the development of new drugs targeting metabolic disorders. Its antioxidant properties and protective effects against oxidative stress make it a valuable component in the creation of medications aimed at treating conditions like diabetes and obesity.
Used in Nutraceutical Industry:
In the nutraceutical sector, 5,5-dimethylthiazolidine-4-carboxylic acid is utilized as an ingredient in dietary supplements and functional foods. Its potential antioxidant capabilities and research into metabolic disorder treatment positions it as a beneficial addition to products designed to support health and wellness.

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

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

Downstream Products

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

Relevant academic research and scientific papers

'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.

Chemistry of diazafulvenium methides in the synthesis of functionalized pyrazoles

(Chemical Equation Presented) The chemistry of diazafulvenium methides generated by the thermal extrusion of sulfur dioxide from 2,2-dioxo-1H,3H- pyrazolo[1,5-c] [1,3]thiazoles is described. The diazafulvenium methides unsubstituted at C-7 participate in [8π + 2π] cycloadditions giving pyrazolo-annulated heterocycles resulting from the addition across the 1,7-position. 1-Mefhyl-diazafulvenium methides and 7,7-dimethyl-diazafulvenium methides undergo intramolecular sigmatropic [1,8]H shifts giving vinyl- 1H-pyrazoles.

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.

DERIVATIVES OF THIAZOLIDINECARBOXYLIC ACIDS AND RELATED ACIDS

New substituted derivatives of thiazolidine-, thiazane-and related carboxylic acids which have the general formula STR1 are useful as angiotensin converting enzyme inhibitors.