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

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

Uses

Used in Pharmaceutical Research:
BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is used as a synthetic intermediate for the development of new drugs and bioactive compounds, leveraging its unique structural properties to enhance the therapeutic potential of various medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is utilized as a key component in the design and synthesis of novel therapeutic agents, contributing to the advancement of drug discovery and innovation.
Used in Antiviral and Antibacterial Applications:
BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is studied for its potential antiviral and antibacterial properties, making it a promising candidate for the development of new treatments against infectious diseases.
Used in Drug Development:
BOC-(R)-5,5-DIMETHYLTHIAZOLIDINE-4-CARBOXYLIC ACID is employed as a building block in the creation of innovative pharmaceuticals, with its unique chemical structure offering new avenues for the treatment of various medical conditions.

Upstream product

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

Downstream Products

• 321434-78-0 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester 
• 1026403-24-6 5,5-dimethyl-4-(2-trifluoromethyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester 
• 858780-77-5 4-(2-methoxy-benzylcarbamoyl)-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 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 
• 858780-76-4 5,5-dimethyl-4-(N'-methyl-N'-phenyl-hydrazinocarbonyl)-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 

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.

Design and synthesis of highly potent HIV protease inhibitors with activity against resistant virus

A series of highly potent HIV protease inhibitors have been designed and synthesized. These compounds are active against various clinical viral isolates as well as wild-type virus. The synthesis and biological activity of these HIV protease inhibitors are discussed.

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.

Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine

We designed and synthesized a new class of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy- 4-phenylbutyric acid], with a hydroxymethylcarbonyl (HMC) isostere as the active moiety. A systematic evaluation of structure - activity relationships for HIV protease inhibition, anti-HIV activities, and pharmacokinetic profiles has led to the delineation of a set of structural characteristics that appear to afford an orally available HIV protease inhibitor. Optimum structures, exemplified by 21f (JE-2147), incorporated 3-hydroxy-2- methylbenzoyl groups as the P2 ligand, (R)-5,5-dimethyl-1,3-thiazolidine-4- carbonyl (Dmt) residue at the P1' site, and 2-methylbenzylcarboxamide group as the P2' ligand. The present study demonstrated that JE-2147 has potent antiviral activities in vitro and exhibits good oral bioavailability and plasma pharmacokinetic profiles in two species of laboratory animals.

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