42258-90-2

Basic information

• Product Name: methyl (R)-thiazolidine-4-carboxylate
• Synonyms: methyl (R)-thiazolidine-4-carboxylate;4-Thiazolidinecarboxylicacid,methylester,(4R)-(9CI);(4R)-Thiazolidine-4-carboxylic acid methyl ester;(R)-4α-Thiazolidinecarboxylic acid methyl ester;(R)-Thiazolidine-4α-carboxylic acid methyl ester;(R)-methyl thiazolidine-4-carboxylate;methyl (4R)-1,3-thiazolidine-4-carboxylate
• CAS NO: 42258-90-2
• Molecular Formula: C₅H₉NO₂S
• Molecular Weight: 147.19546
• EINECS: 255-739-3
• Product Categories: CARBOXYLICESTER
• Mol File: 42258-90-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 238.9 °C at 760 mmHg
• Flash Point: 98.3 °C
• Appearance: /
• Density: 1.208 g/cm³
• Vapor Pressure: 0.0413mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: methyl (R)-thiazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R)-thiazolidine-4-carboxylate(42258-90-2)
• EPA Substance Registry System: methyl (R)-thiazolidine-4-carboxylate(42258-90-2)

Safety Data

• Hazardous Substances Data: 42258-90-2(Hazardous Substances Data)

Usage

General Description

Methyl (R)-thiazolidine-4-carboxylate is a chemical compound that is derived from thiazolidine-4-carboxylic acid. It is commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds. methyl (R)-thiazolidine-4-carboxylate has a thiazolidine ring structure, containing a sulfur atom and a carbon-carbon double bond, and is chiral, meaning it has a non-superimposable mirror image. The (R) configuration in the name indicates the stereochemistry of the molecule, specifying the spatial arrangement of its atoms. Methyl (R)-thiazolidine-4-carboxylate is known for its potential pharmacological activity, particularly in the development of drugs targeting conditions such as diabetes and obesity. Its unique structure and properties make it a valuable tool in the field of medicinal chemistry and drug discovery.

InChI:InChI=1/C5H9NO2S/c1-8-5(7)4-2-9-3-6-4/h4,6H,2-3H2,1H3/t4-/m0/s1

Upstream product

• 34592-47-7 L-thioproline 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 52-89-1 l-cysteine hydrochloride 
• 2485-62-3 L-Cysteine methyl ester 
• 67089-84-3 (R)-thiazolidine-4-carboxylic acid hydrochloride 
• 110-88-3 1,3,5-Trioxan 
• 5714-80-7 D-cysteine methyl ester hydrochloride 
• 18598-63-5 L-cysteine methyl ester hydrochloride 

Downstream Products

• 86634-64-2 (R)-6-phenyl-5-thioxotetrahydroimidazo[1,5-c]thiazol-7(3H)-one 
• 479586-30-6 (R)-3-[(R)-3-tert-Butoxycarbonylamino-4-(2-fluoro-phenyl)-butyryl]-thiazolidine-4-carboxylic acid methyl ester 
• 156320-26-2 (R)-Thiazolidine-4-carboxylic acid hydrazide 
• 59418-09-6 4-thiazolecarboxylate methyl ester 
• 105126-41-8 chloro-3 nitro-5 indazole 
• 105126-40-7 (R)-6-Cyclohexyl-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 105126-43-0 (R)-6-(4-Methoxy-phenyl)-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 105126-42-9 (R)-6-p-Tolyl-dihydro-imidazo[1,5-c]thiazole-5,7-dione 
• 51977-23-2 6,8-dioxo-7-phenyl-3-thia-1,7-diazabicyclo<3.3.0>octane 
• 105126-44-1 (R)-6-(4-Chloro-phenyl)-dihydro-imidazo[1,5-c]thiazole-5,7-dione 

Relevant articles and documents

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Method for preparing thiazole-4-formic acid

The invention discloses a method for preparing thiazole-4-formic acid. By the aid of the method, the problems of relatively high prices of raw materials used in old processes for thiabendazole which is one of important traditional pesticide and bactericide varieties and low yield of the thiabendazole can be solved. The method includes steps of generating thiazolidine-4-formic acid from L-cysteinehydrochloride, formaldehyde and pyridine; carrying out reaction on the thiazolidine-4-formic acid, methyl alcohol and HCl gas to generate thiazolidine-4-methyl formate; carrying out reaction on the thiazolidine-4-methyl formate, acetonitrile and MnO2 to generate thiazole-4-methyl formate; hydrolyzing the thiazole-4-methyl formate under the effect of sodium hydroxide to obtain the thiazole-4-formicacid which is a product. The method has the advantages of simple process synthetic route, mild reaction condition, low cost, environmental protection, safety, excellent application prospect, good social benefit and high economic benefit.

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.