82938-50-9

Basic information

• Product Name: (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID
• Synonyms: (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID;(4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-CARBOXYLIC ACID;(4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-2-caroxylic acid.;1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid;(4S)-N-(tert-Butyldimethylsilyl)azetidin-2-one-4-carboxylic acid,99%;2-Azetidinecarboxylicacid, 1-[(1,1-dimethylethyl)dimethylsilyl]-4-oxo-, (2S)-;(2S)-1-(tert-butyl(Dimethyl)silyl)-4-oxo-azetidine-2-carboxylic acid;1-(Tert-Butyl-Dimethyl-Silanyl)-4-Oxo-Azetidine-2-Carboxylic Acid(WX625082)
• CAS NO: 82938-50-9
• Molecular Formula: C₁₀H₁₉NO₃Si
• Molecular Weight: 229.35
• Mol File: 82938-50-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 135-137 °C
• Boiling Point: 309.312°C at 760 mmHg
• Flash Point: 140.867°C
• Appearance: /solid
• Density: 1.091g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID(82938-50-9)
• EPA Substance Registry System: (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID(82938-50-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• Hazardous Substances Data: 82938-50-9(Hazardous Substances Data)

Usage

General Description

(4S)-N-(tert-butyldimethylsilyl)azetidin-2-one-4-carboxylic acid is a chemical compound with the molecular formula C11H19NO3Si. It is an azetidin-2-one derivative with a carboxylic acid functional group. (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID is often used as a building block in the synthesis of pharmaceuticals and other organic compounds. The tert-butyldimethylsilyl (TBS) group is a common protecting group used in organic synthesis to protect sensitive functional groups from unwanted reactions. (4S)-N-(TERT-BUTYLDIMETHYLSILYL)AZETIDIN-2-ONE-4-CARBOXYLIC ACID may also have potential applications in medicinal chemistry and drug development due to its unique structure and functional group composition.

InChI:InChI=1/C10H19NO3Si/c1-10(2,3)15(4,5)11-7(9(13)14)6-8(11)12/h7H,6H2,1-5H3,(H,13,14)/t7-/m0/s1

Upstream product

• 130540-09-9 dibenzyl (S)-2-(tert-butyldimethylsilylamino)succinate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 82938-49-6 benzyl (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 
• 185387-26-2 (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 

Downstream Products

• 164201-53-0 (3S,4R)-3-benzyl-3-ethyl-1-(tert-butyldimethylsilyl)-2-oxoazetidine-4-carboxylic acid 
• 939391-38-5 (R)-1-(tert-butyldimethylsilyl)-N-((R)-1-(3-fluoro-4-methoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-4-oxoazetidine-2-carboxamide 
• 236123-21-0 benzyl [(S)-1-[N-(tert-butyldimethylsilyl)-4-oxo-azetidine-2-carbonyl]amino]-cyclopropanecarboxylate 
• 926630-08-2 C₃₃H₃₆N₂O₄Si 
• 185387-26-2 (2R)-benzyl N-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate 
• 342624-65-1 (4S)-4-benzyloxycarbonyl-1-(tert-butyldimethylsilyl)-3-[Z-4'-(tert-butyldiphenylsilyloxy)phenylmethylene]-2-azetidinone 
• 193959-24-9 (4S)-4-benzyloxycarbonyl-1-(tert-butyldimethylsilyl)-3-[E-4'-(tert-butyldiphenylsilyloxy)phenylmethylene]-2-azetidinone 

Relevant articles and documents

QUATERNARY LACTAM COMPOUND AND PHARMACEUTICAL USE THEREOF

A quaternary lactam compound of formula (I). The compound is used in the manufacture of a medicament for the treatment and/or prevention of thrombotic or thromboembolic disorders.

Stereoselective Synthesis of Tricyclic Diproline Analogues that Mimic a PPII Helix: Structural Consequences of Ring-Size Variation

Polycyclic proline-derived scaffolds (ProMs) have recently demonstrated their value as conformationally defined dipeptide analogs for the modular construction of secondary structure mimetics, specifically interfering with PPII helix-mediated protein-protein interactions. We disclose the stereoselective synthesis of two new tricyclic amino acid scaffolds (ProM-4 and ProM-8) that differ from the first generation scaffold ProM-1 by the size of ring A. Conformational preferences and subtle structural differences of the three homologous scaffolds were analyzed by X-ray crystallography, computational calculations, and NMR spectroscopy. N-tert-butoxycarbonyl(Boc)-3-(1-propenyl)azetidine-2-carboxylic acid was prepared from L-aspartic acid through β-lactam intermediates. The corresponding piperidine-based building block rac-N-Boc-3-vinylpipecolic acid was synthesized by Cu-catalyzed 1,4-addition of vinyl-MgBr to methyl N-Boc-2,3-dehydropipecolate. Target molecules were prepared through peptide coupling of the respective ring A building blocks with cis-5-vinylproline tert-butyl ester and subsequent ring-closing metathesis. Selective deprotection of a tert-butyl carbamate (N-Boc protecting group) in the presence of a tert-butyl ester was achieved with trifluoroacetic acid at 0 C. Two new tricyclic amino acid scaffolds, which differ from the first generation scaffold by the size of ring A, were stereoselectively synthesized. The conformational analysis of the three homologous scaffolds was revealed by NMR spectroscopy.

β-Lactam derivatives as enzyme inhibitors: N-substituted derivatives of (S)-4-oxoazetidine-2-carboxylate as inhibitors of elastase and papain

N-Alkyl and N-acyl substituted 4-oxoazetidine-2-carboxylates are synthesized and evaluated as inhibitors of the proteases porcine pancreatic elastase (PPE) and papain. The compounds are obtained by alkylation or acylation at the nitrogen of benzyl (S)-4-oxoazetidine-2-carboxylate, which is synthesized by a modified literature procedure. The enzymatic assays prove some derivatives to be effective inhibitors of PPE and/or papain. The N-BOC protected amino acid derivatives 10 and 13 inhibit PPE reversibly with K(I)-values in the micromolar range. On the other hand, papain is inactivated irreversibly by benzyl (S)-2-(benzyloxycarbonyl)azetidin-1-acetate (6).