148312-55-4

Basic information

• Product Name: tert-Butyl thiazolidine-3-carboxylate
• Synonyms: tert-Butyl thiazolidine-3-carboxylate
• CAS NO: 148312-55-4
• Molecular Formula: C₈H₁₅NO₂S
• Molecular Weight: 189.2752
• Mol File: 148312-55-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 266.3±33.0 °C(Predicted)
• Appearance: /
• Density: 1.137±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -1.67±0.20(Predicted)
• CAS DataBase Reference: tert-Butyl thiazolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl thiazolidine-3-carboxylate(148312-55-4)
• EPA Substance Registry System: tert-Butyl thiazolidine-3-carboxylate(148312-55-4)

Safety Data

• Hazardous Substances Data: 148312-55-4(Hazardous Substances Data)

Usage

General Description

Tert-Butyl thiazolidine-3-carboxylate is a synthetic chemical compound that belongs to the thiazolidine family. It is formed from a thiazolidine ring and a carboxylate group. This chemical is often used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its versatile reactivity and potential biological activity. The tert-butyl group attached to the thiazolidine ring provides stability and sterically hinders certain reactions, making it a valuable molecule in the development of various organic compounds. However, it is important to handle this chemical with care and in accordance with safety guidelines due to its potential hazards.

Upstream product

• 504-78-9 1,3-thiazolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 173604-22-3 N-(tert-butoxycarbonyl)thiazolidin-4-one 
• 177779-62-3 4-Acetoxy-thiazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 83461-64-7 (R)-α-acetoxyphenylacetaldehyde 
• 83461-63-6 (S)-α-acetoxyphenylacetaldehyde 
• 752212-30-9 (1'R,2R)-tert-butyl 2-(1-acetoxy-1-phenylmethyl)thiazolidine-3-carboxylate 
• 752212-32-1 (1'R,2R)-tert-butyl 2-[1-acetoxy-1-(4-methoxyphenyl)methyl]thiazolidine-3-carboxylate 
• 752212-22-9 (1'S,2R)-tert-butyl 2-[1-acetoxy-1-(4-methoxyphenyl)methyl]thiazolidine-3-carboxylate 
• 108104-23-0 (S)-hexahydromandelaldehyde acetate 
• 851292-66-5 (R)-2-((R)-Acetoxy-cyclohexyl-methyl)-thiazolidine-3-carboxylic acid tert-butyl ester 
• 59411-58-4 (R)-1-cyclohexylethane-1,2-diol 
• 61414-09-3 (S)-1-cyclohexyl-1,2-ethanediol 

Relevant articles and documents

Model syntheses of thiazolidine nucleoside analogues

The syntheses of racemic thiazolidinyl thymine and cytosine derivatives 6a and 6b, and 10a and 10b, prototypes of a novel family of heterosubstituted nucleosides, have been achieved from rhodanine (3) or thiazolidine (7) by a short sequence of steps. The key reaction involved efficient coupling of silylated thymine and cytosine to N-Boc-protected 4- and 5- acetoxythiazolidines, 5 and 9, assisted by tert-butyldimethylsilyl trifluoro- methanesulfonate.

Enantioselective reaction of α-lithiated thiazolidines as new chiral formyl anion equivalents

The reaction of lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine with benzophenone in the presence of (-)-sparteine afforded the products with up to 97% ee and 93% ee, respectively. The reaction with various aromatic and aliphatic aldehydes also afforded the products with high enantioselectivity and moderate diastereoselectivity. Each diastereomer could be converted to optically active diols. Consequently, lithiated N-Boc-thiazolidine and N-Boc-benzothiazolidine serve as chiral formyl anion equivalents. The reaction was confirmed to proceed through a dynamic thermodynamic resolution pathway.