19907-59-6

Usage

Uses

Used in Pharmaceutical Industry:
L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its chiral nature makes it a valuable building block for the development of enantiomerically pure drugs, which can have significant implications in terms of efficacy and safety.
Used in the Preparation of Bicyclomycin:
Specifically, L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester is utilized in the preparation of bicyclomycin, a potent antibiotic with broad-spectrum activity against various bacterial pathogens. The compound's role in the synthesis process highlights its importance in the development of new and effective treatments for bacterial infections.

Upstream product

• 67-56-1 methanol 
• 52-90-4 L-Cysteine 
• 67-64-1 acetone 
• 2485-62-3 L-Cysteine methyl ester 
• 5714-80-7 D-cysteine methyl ester hydrochloride 
• 18598-63-5 L-cysteine methyl ester hydrochloride 
• 186581-53-3 diazomethane 
• 58166-38-4 2,2-dimethyl-thiazolidine-4(R)-carboxylic acid 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 100429-04-7 3-benzoyl-2,2-dimethyl-5-hydroxy-4-methoxycarbonylthiazolidine 
• 67089-83-2 3-benzoyl-2,2-dimethyl-4(R)-methoxycarbonylthiazolidine 

Relevant academic research and scientific papers

Design, synthesis, and safener activity of novel methyl (r)-n-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates

A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from L-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR,1H NMR,13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.

D-Penicillamine and L-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols

D-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous L-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes, resulting in very good, albeit slightly lower selectivities, up to 89%. The combined use of these two types of thiazolidines constitutes a very interesting strategy for synthesizing both (S) and (R) enantiomers of chiral secondary alcohols, thus leading the way to a myriad of useful optically active products with opposite absolute configurations.

Modular chiral thiazolidine catalysts in asymmetric aryl transfer reactions

Modular chiral thiazolidine derivatives were synthesized in a single step from inexpensive and commercially available starting materials. These ligands catalyzed enantioselective arylation of different aldehydes using aryl boronic acids as a source of transferable aryl groups. The products were obtained in excellent yields and good enantioselectivities.

The steric effect and enantioselectivity of chiral 2,2-disubstituted thiaprolinol derivatives as ligands for borane reduction of aromatic ketones and for diethylzinc addition to aromatic aldehydes

A new series of chiral amino alcohols 3a-e has been prepared from natural amino acid L-cysteine. These compounds have been used as chiral ligands for borane reduction of ketones and for diethylzinc addition to aldehydes. In the reduction of ketones, 3b-e have been used as the substitute of (R)-prolinol to provide (S)-alcohols in good yields had modest enantioselectivity (30-50% ee). In the diethylzinc addition to aldehydes, 3b-e promoted the formation of (S)-alcohols in excellent yields and medium to good enantioselectivities (60-80% ee). Copyright (C) 1996 Published by Elsevier Science Ltd.

'Hidden' Axial Chirality as a Stereodirecting Element in Reactions Involving Enol(ate) Intermediates. Part 1. Cyclisation Reactions of Methyl (4R)-3-(2-Diazo-3-oxobutanoyl)thiazolidine-4-carboxylate and Related Compounds

Methyl (4R)-3-(2-diazo-3-oxobutanoyl)thiazolidine-4-carboxylate 1b underwent cyclisation, under a variety of basic conditions, to give methyl (6S)-2-oxo-8-thia-1,4,5-triazabicyclonon-3-ene-6-carboxylate 2a in an enantiopure state.The absolute configuration of compound 2a was deduced by X-ray crystallography.Similar stereoselective cyclisations, proceeding with retention of configuration, were observed with methyl (4R)-3-thiazolidine-4-carboxylate 1g (to give compound 5a), methyl (4R)-3-(2-diazo-3-oxobutanoyl)-2,2-dimethylthiazolidine-4-carboxylate 20a (to give compound 21a) and methyl (2R,4R)-3-(2-diazo-3-oxobutanoyl)-2-methylthiazolidine-4-carboxylate 22a (to give compound 24).An X-ray crystallographic analysis of compound 22a revealed that the amide and diazo ketone units, although individually near planar, were twisted from each other by 35 deg; it was notable that the amide linkage adopted the (Z)-geometry required for the cyclisation reaction whereas the diazo moiety was incorrectly aligned.It is suggested that the cyclisation reactions proceed by way of planar enol(ate) intermediates, e.g. 6a, which possess axial chirality.