117918-23-7

Basic information

• Product Name: BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID
• Synonyms: (R)-BOC-5,5-DIMETHYL-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID;(R)-BOC-DTC;N-ALPHA-T-BUTYLOXYCARBONYL-L-5,5-DIMETHYL-THIAZOLIDINE;BOC-L-DMTA;BOC-L-DTC-OH;BOC-(R)-5,5-DIMETHYL-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID;BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-5,5-DIMETHYL-THIAZOLIDINE
• CAS NO: 117918-23-7
• Molecular Formula: C₁₁H₁₉NO₄S
• Molecular Weight: 261.34
• Mol File: 117918-23-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Store at 0-5°C
• CAS DataBase Reference: BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(117918-23-7)
• EPA Substance Registry System: BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID(117918-23-7)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 117918-23-7(Hazardous Substances Data)

Usage

General Description

BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is a chemical compound with potential applications in medicinal chemistry and drug development. It is a derivative of the amino acid cysteine and contains a BOC (tert-butyloxycarbonyl) protective group. BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID has been used in the synthesis of peptides and small molecules for pharmaceutical research. It has also been studied for its potential as a building block in the development of new drugs and bioactive compounds. Additionally, BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID may have antiviral and antibacterial properties, making it a subject of interest for further investigation in the field of pharmaceutical science.

Upstream product

• 85929-61-9 methyl (+/-)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1113-41-3 L-penicillamine 
• 15260-83-0 5,5-dimethyl-thiazolidine-4-carboxylic acid 
• 52-66-4 DL-Penicillamin 
• 72778-00-8 (R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 72778-00-8 5,5-dimethylthiazolidine-4-carboxylic acid 

Downstream Products

• 858780-78-6 4-(2-ethoxy-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-88-8 4-(4-methoxycarbonyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-87-7 4-(4-carbamoyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-86-6 4-(3-methoxycarbonyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-85-5 4-(3-carbamoyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-56-0 5,5-dimethyl-4-(1-methyl-1-phenyl-ethylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester 
• 321435-46-5 (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid (3,5-dimethyl-isoxazol-4-ylmethyl)-amide 
• 321435-42-1 (R)-3-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((3S,4S)-3-hydroxy-chroman-4-ylcarbamoyl)-5-phenyl-pentanoyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,6-dimethyl-benzylamide 
• 321435-41-0 (2R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-5-[(R)-4-(2,6-dimethyl-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-5-oxo-pentanoic acid 

Relevant articles and documents

Design and synthesis of several small-size HTLV-I protease inhibitors with different hydrophilicity profiles

The human T cell leukemia/lymphotropic virus type 1 (HTLV-I) is clinically associated with adult T cell leukemia/lymphoma, HTLV-I associated myelopathy/tropical spastic paraparesis, and a number of other chronic inflammatory diseases. To stop the replication of the virus, we developed highly potent tetrapeptidic HTLV-I protease inhibitors. In a recent X-ray crystallography study, several of our inhibitors could not form co-crystal complexes with the protease due to their high hydrophobicity. In the current study, we designed, synthesized and evaluated the HTLV-I protease inhibition potency of compounds with hydrophilic end-capping moieties with the aim of improving pharmaceutic and pharmacokinetic properties.

A concise synthesis of (2S,3S)-BocAHPBA and (R)-BocDMTA, chiral building blocks for peptide-mimetic HIV protease inhibitors

Scalable syntheses of (2S,3S)-3-N-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (BocAHPBA) 1 and (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid (BocDMTA) 2 have been developed. Both 1 and 2 can serve as chiral building blocks in assembling JE-2147 (KNI-764) 3, a potent HIV protease inhibitor. The synthesis of (2S,3S)-BocAHPBA 1 is achieved in 41% overall yield from (S)-2-N,N-dibenzylamino-3-phenylpropanal 4 in five steps where Tamao's reagent [Me2(i-PrO)SiCH2MgCl] is employed for a one-carbon homologation, and Zhao's oxidation protocol (TEMPO, NaClO2, NaClO) is applied to convert a 1,2-glycol moiety into an α-hydroxy acid motif. (R)-BocDMTA 2 is synthesized with 99.4% ee in 24% yield via enantioselective hydrolysis of methyl (±)-5,5-dimethyl-1,3-thiazolidine-4-carboxylate 8b by a Klebsiella oxytoca hydrolase; the unreacted (S)-ester 8b can be recovered and racemized with NaOMe to afford (±)-8b in 46% yield for another round of the enzymatic processing.

Potent Angiotensin II Antagonists with Non-β-branched Aminoacids in Position 5

Amino acids with lipophilic side chains that contain more than one functional group on the β-carbon, i.e. a β-branched hydrocarbon moiety, are required in position 5 of angiotensin II (AII) analogue with potent agonist activity.This requirement for agonis