174740-81-9

Basic information

• Product Name: 1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID
• Synonyms: 1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID;1,2-Azetidinedicarboxylic acid, 1-(phenylMethyl) ester;1-Cbz-azetidine-2-carboxylic acid;1-Benzyl azetidine-1,2-dicarboxylate
• CAS NO: 174740-81-9
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.238
• Mol File: 174740-81-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID(174740-81-9)
• EPA Substance Registry System: 1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID(174740-81-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 174740-81-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Benzyloxycarbonylazetidine-2-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex molecular structures that can have therapeutic effects.
Used in Agrochemical Production:
In the agrochemical industry, 1-Benzyloxycarbonylazetidine-2-carboxylic acid is utilized as a versatile building block in the creation of compounds that can be used in pest control and crop protection due to its reactivity and potential to form various functionalized azetidines.
Used in Drug Discovery:
1-Benzyloxycarbonylazetidine-2-carboxylic acid is employed as a valuable target in drug discovery processes because of its unique pharmacological properties, which can be harnessed to develop new therapeutic agents.
Used in Materials Science:
1-BENZYLOXYCARBONYLAZETIDINE-2-CARBOXYLIC ACID also finds application in materials science, where its structural features can be exploited to create new materials with specific properties, such as improved stability or reactivity in various chemical processes.

Upstream product

• 501-53-1 benzyl chloroformate 
• 2517-04-6 Azetidine-2-carboxylic acid 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 25654-51-7 (2R,2S)-1-benzyloxycarbonylazetidine-2-carboxylic acid 
• 25654-52-8 (2S)-1-(benzyloxycarbonyl)azetidine-2-carboxylic acid 
• 144062-03-3 (S)-4,4-Diphenyl-3-oxa-1-aza-bicyclo[3.2.0]heptan-2-one 
• 144062-03-3 (R)-4,4-Diphenyl-3-oxa-1-aza-bicyclo[3.2.0]heptan-2-one 
• 144062-01-1 (R)-Azetidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 144062-00-0 N-benzyloxycarbonyl azetidine-2-carboxylate methyl ester 
• 144062-05-5 (S)-2-(Hydroxy-diphenyl-methyl)-azetidine-1-carboxylic acid benzyl ester 
• 144062-02-2 (R)-2-(Hydroxy-diphenyl-methyl)-azetidine-1-carboxylic acid benzyl ester 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 

Relevant articles and documents

Methods for producing N-protected-azetidine-2-carboxylic acids

There is disclosed a method for producing an essentially enantiomerically pure N-protected-azetidine-2-carboxylic acid of formula (1): which method is characterized by: subjecting a crude enantiomerically excess N-protected-azetidine-2-carboxylic acid comprising said enantiomer represented by formula (1) in excess to the other enantiomer thereof to crystallization in an organic solvent selected from aromatic hydrocarbon, aliphatic ether, aliphatic alcohol, aliphatic ketone, aliphatic nitrile, aliphatic amide, aliphatic sulfoxide, aliphatic ester and a mixed solvent thereof, wherein R is: an optionally substituted alkyl, alicyclic or alicyclicalkyl group, an optionally substituted alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, or a dialkylamino group, and absolute configuration of the asterisked asymmetric carbon atom is S or R.

Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors

Recent evidence indicating the therapeutic potential of cholinergic channel modulators for the treatment of central nervous system (CNS) disorders as well as the diversity of brain neuronal nicotinic acetylcholine receptors (nAChRs) have suggested an opportunity to develop subtype-selective nAChR ligands for the treatment of specific CNS disorders with reduced side effect liabilities. We report a novel series of 3-pyridyl ether compounds which possess subnanomolar affinity for brain nAChRs and differentially activate subtypes of neuronal nAChRs. The synthesis and structure-activity relationships for the leading members of the series are described, including A-85380 (4a), which possesses ca. 50 pM affinity for rat brain [3H]-(- )cytisine binding sites and 163% efficacy compared to nicotine to stimulate ion flux at human α4β2 nAChR subtype, and A-84543 (2a), which exhibits 84- fold selectivity to stimulate ion flux at human α4β2 nAChR subtype compared to human ganglionic type nAChRs. Computational studies indicate that a reasonable superposition of a low energy conformer of 4a with (S)-nicotine and (-)-epibatidine can be achieved.

Enantioselective catalytic reductions of ketones with new four membered oxazaborolidines: Application to (S)-tetramisole

Enantioselective catalytic reduction of ketones with both the enantiomers of new four membered oxazaborolidines is described.