189228-43-1

Basic information

• Product Name: 4-Thiazolidinecarboxylic acid, 2-phenyl-, ethyl ester, (4R)-
• CAS NO: 189228-43-1
• Molecular Formula: C12H15NO2S
• Molecular Weight: 237.323
• Mol File: 189228-43-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinecarboxylic acid, 2-phenyl-, ethyl ester, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinecarboxylic acid, 2-phenyl-, ethyl ester, (4R)-(189228-43-1)
• EPA Substance Registry System: 4-Thiazolidinecarboxylic acid, 2-phenyl-, ethyl ester, (4R)-(189228-43-1)

Safety Data

• Hazardous Substances Data: 189228-43-1(Hazardous Substances Data)

Upstream product

• 196930-46-8 (4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid 
• 64-17-5 ethanol 
• 100-52-7 benzaldehyde 
• 3411-58-3 L-cystein ethyl ester 
• 868-59-7 L-cysteine ethyl ester hydrochloride 

Downstream Products

• 209627-19-0 (R)-3-(3-Amino-pyrazine-2-carbonyl)-2-phenyl-thiazolidine-4-carboxylic acid ethyl ester 
• 157020-34-3 (2R,4R)-4-formyl-2-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 161458-78-2 (2R,4R)-4-(hydroxymethyl)-2-phenylthiazolidine-3-carboxylic acid tert-butyl ester 
• 449729-42-4 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid methyl ester 
• 449729-39-9 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-hydroxy-6-oxoheptanoic acid 
• 449729-44-6 (S)-7-[(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidin-4-yl]-7-methoxycarbonyloxy-6-oxoheptanoic acid methyl ester 
• 452100-77-5 (2R,4R)-4-(Cyano-trimethylsilanyloxy-methyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 3411-58-3 L-cystein ethyl ester 
• 155346-60-4 methyl 5,5-dimethyl-2-phenylthiazolidine-4-carboxylate 
• 78979-47-2 (4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate 
• 1174759-03-5 (4R) ethyl 2-(3-methylphenyl)thiazolidine-4-carboxylate 
• 78979-46-1 (4R) ethyl 2-(4-methoxyphenyl)thiazolidine-4-carboxylate 
• 368427-19-4 (4R) ethyl 2-(4-methylphenyl)thiazolidine-4-carboxylate 
• 164986-94-1 (2R,4R)-4-(hydroxymethyl)-2-phenylthiazolidine 

Relevant articles and documents

Protected Derivatives of (R)-Cysteine and (R)-Cysteinol

The synthesis of N, O, S protected forms of (R)-cysteine and (R)-cysteinol as bicyclic derivatives is described.The reactivity and the preparation of substituted derivatives of these systems is also discussed.

Reversible thiazolidine exchange: A new reaction suitable for dynamic combinatorial chemistry

New dynamic combinatorial libraries (DCLs) were generated using the reversible aminothiol exchange reaction of thiazolidines and aromatic aldehydes. The reaction proceeded in aqueous buffered media at pH 4 and room temperature to generate thermodynamically controlled mixtures of heterocycles. The synthesis of an enantiomerically pure thiazolidinyloxazolidine is also reported. The oxazolidine moiety could be exchanged in CH2Cl2 in the presence of catalytic p-TsOH.

A novel synthesis of (+)-biotin from L-cysteine

(+)-Biotin (1) was synthesized in 25% overall yield over 11 steps from L-cysteine. The contiguous asymmetric centers at C-3a and C-6a were formed through a novel and highly stereoselective Lewis base-catalyzed cyanosilylation of α-amino aldehyde 3 to provide anti- O-TMS-cyanohydrin 4 with high stereoselectivity and in high yield (anti/syn = 92:8, 96%). Treatment of 4 with a di-Grignard reagent, 1,4-bis(bromomagnesio)butane, followed by carbon dioxide, efficiently installed the 4-carboxybutyl chain at C-4 to give keto acid 5. The final cyclization to bicyclic compound 7b, a precursor to 1, was realized by a palladium-catalyzed intramolecular allylic amination of cis-allylic carbonate 6b that was elaborated from 5.