19907-59-6

Basic information

• Product Name: L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester
• Synonyms: L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester;AMHPVDWIPMNOSV-YFKPBYRVSA-N
• CAS NO: 19907-59-6
• Molecular Formula: C₇H₁₃NO₂S
• Molecular Weight: 175.24862
• Product Categories: Heterocycles, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 19907-59-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester(19907-59-6)
• EPA Substance Registry System: L-2,2-DiMethylthiazolidine-4-carboxylic Acid Methyl Ester(19907-59-6)

Safety Data

• Hazardous Substances Data: 19907-59-6(Hazardous Substances Data)

Usage

Uses

L-2,2-Dimethylthiazolidine-4-carboxylic Acid Methyl Ester is a chiral thiazolidine used in the preparation of bicyclomycin.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

'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.