CAS 72776-05-7

(S)-Benzyl 2-azetidinone-4-carboxylate

Description:

(S)-Benzyl 2-azetidinone-4-carboxylate, with the CAS number 72776-05-7, is a chiral compound that belongs to the class of azetidinones, which are four-membered cyclic amides. This substance features a benzyl group attached to the nitrogen atom of the azetidinone ring, as well as a carboxylate functional group at the 4-position of the ring. The presence of the chiral center at the 2-position contributes to its stereochemical properties, making it of interest in asymmetric synthesis and pharmaceutical applications. Typically, compounds like this exhibit moderate solubility in organic solvents and may have specific reactivity patterns due to the functional groups present. The compound's structure allows for potential interactions in biological systems, which can be explored for medicinal chemistry purposes. Its synthesis and characterization are important for applications in drug development, particularly in the design of compounds with specific biological activities. As with many azetidinones, it may also serve as a building block in the synthesis of more complex molecules.

Formula: C₁₁H₁₁NO₃

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-/m0/s1

SMILES: c1ccc(cc1)COC(=O)[C@@H]1CC(=N1)O

Synonyms:

• Benzyl (S)-4-oxo-2-azetidinecarboxylate
• Trans-Tert-Butyl 6-Amino-3-Azabicyclo[3.1.0]Hexane-3-Carboxylate
• (S)-benzyl 4-oxoazetidine-2-carboxylate
• benzyl (2S)-4-oxoazetidine-2-carboxylate

(S)-Benzyl 4-oxoazetidine-2-carboxylate

CAS: 72776-05-7

Formula: C₁₁H₁₁NO₃

Purity: 97%

Color and Shape: Solid

Molecular weight: 205.2099

Ref: IN-DA003CMX

Benzyl (S)-(−)-4-Oxo-2-Azetidinecarboxylate

CAS: 72776-05-7

Benzyl (S)-(−)-4-Oxo-2-Azetidinecarboxylate

Purity: 97%

Molecular weight: 205.21g/mol

Ref: 54-OR1027634

Benzyl (S)-4-oxo-2-azetidinecarboxylate

CAS: 72776-05-7

Benzyl (S)-4-oxo-2-azetidinecarboxylate is a reversible inhibitor of porcine pancreatic trypsin and chymotrypsin. It irreversibly inhibits the proteases, papain and bromelain. Benzyl (S)-4-oxo-2-azetidinecarboxylate is an alkylating agent that binds to the sulfhydryl group of enzymes, inactivating them by forming covalent bonds with cysteine residues. This irreversible inhibition leads to a decrease in protein synthesis and cell death.

Formula: C₁₁H₁₁NO₃

Purity: Min. 98 Area-%

Color and Shape: White Powder

Molecular weight: 205.21 g/mol

Ref: 3D-FB11211

(S)-Benzyl 4-oxoazetidine-2-carboxylate

CAS: 72776-05-7

Formula: C₁₁H₁₁NO₃

Purity: 97%

Molecular weight: 205.213

Ref: 10-F219752

Benzyl (2S)-4-Oxoazetidine-2-carboxylate

Controlled Product

CAS: 72776-05-7

Applications benzyl (2s)-4-oxoazetidine-2-carboxylate, is a building block used for various chemical synthesis such as for the synthesis of NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors.
References Baldwin, J.E. et al. Tetrahedron 51, 11581-11581, (1995); Hanessian, S. et al. Synlett , 33-33, (1992)

Formula: C₁₁H₁₁NO₃

Color and Shape: Neat

Molecular weight: 205.21

Ref: TR-B535385