95729-87-6

Basic information

• Product Name: (R)-benzyl 4-oxoazetidine-2-carboxylate
• Synonyms: (R)-benzyl 4-oxoazetidine-2-carboxylate;benzyl (2r)-4-oxoazetidine-2-carboxylate;benzyl (R)-4-oxoazetidine-2-carboxylate
• CAS NO: 95729-87-6
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.20994
• Mol File: 95729-87-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 404.7°C at 760 mmHg
• Flash Point: 198.5°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 9.28E-07mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: (R)-benzyl 4-oxoazetidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-benzyl 4-oxoazetidine-2-carboxylate(95729-87-6)
• EPA Substance Registry System: (R)-benzyl 4-oxoazetidine-2-carboxylate(95729-87-6)

Safety Data

• Hazardous Substances Data: 95729-87-6(Hazardous Substances Data)

Usage

General Description

(R)-benzyl 4-oxoazetidine-2-carboxylate is a chemical compound with the molecular formula C13H11NO3. It is a chiral ester, meaning it has a non-superimposable mirror image, and is commonly used in organic synthesis and medicinal chemistry. (R)-benzyl 4-oxoazetidine-2-carboxylate is known for its use in the preparation of various pharmaceuticals and organic molecules. It is also used as a building block in the synthesis of complex chemical compounds. Additionally, (R)-benzyl 4-oxoazetidine-2-carboxylate has potential applications in the development of new drugs and therapeutic molecules due to its unique chemical properties. Overall, this compound is a valuable and versatile component in the field of organic chemistry and drug development.

InChI:InChI=1/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m1/s1

Upstream product

• 2791-79-9 dibenzyl L-aspartate 
• 4079-59-8 D-aspartic acid dibenzyl ester 

Downstream Products

• 209329-11-3 (2R)-2-azetidinylmethanol 
• 98019-65-9 (2R)-2-azetidinone-4-carboxylic acid 
• 185387-26-2 (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 
• 161511-90-6 (R)-1-t-butyloxycarbonyl-2-azetidinemethanol 

Relevant articles and documents

Water-Insensitive Synthesis of Poly-β-Peptides with Defined Architecture

Biocompatible and proteolysis-resistant poly-β-peptides have broad applications and are dominantly synthesized via the harsh and water-sensitive ring-opening polymerization of β-lactams in a glovebox or using a Schlenk line, catalyzed by the strong base LiN(SiMe3)2. We have developed a controllable and water-insensitive ring-opening polymerization of β-amino acid N-thiocarboxyanhydrides (β-NTAs) that can be operated in open vessels to prepare poly-β-peptides in high yields, with diverse functional groups, variable chain length, narrow dispersity and defined architecture. These merits imply wide applications of β-NTA polymerization and resulting poly-β-peptides, which is validated by the finding of a HDP-mimicking poly-β-peptide with potent antimicrobial activities. The living β-NTA polymerization enables the controllable synthesis of random, block copolymers and easy tuning of both terminal groups of polypeptides, which facilitated the unravelling of the antibacterial mechanism using the fluorophore-labelled poly-β-peptide.

Efficient asymmetric synthesis of ABT-594; a potent, orally effective analgesic

A concise asymmetric synthesis of (R)-2-chloro-5-(2- azetidinylmethoxy)pyridine (ABT-594) is presented in which the key intermediate t-butoxycarbonyl protected (2R)-azetidinylalcohol is obtained in three steps from the dibenzyl ester of D-aspartic acid in 44% yield and >99% ee.

4-Substituted-2-azetidinone compound, process of producing the compounds, and medicaments containing the compounds

A novel 4-substituted-2-azetidinone compound shown by the general formula STR1 and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in schizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.