103733-16-0

Basic information

• Product Name: (3R,4S)-3-Isopropyl-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one
• Synonyms: (3R,4S)-3-Isopropyl-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one
• CAS NO: 103733-16-0
• Molecular Weight: 321.419
• Mol File: 103733-16-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R,4S)-3-Isopropyl-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-Isopropyl-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one(103733-16-0)
• EPA Substance Registry System: (3R,4S)-3-Isopropyl-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one(103733-16-0)

Safety Data

• Hazardous Substances Data: 103733-16-0(Hazardous Substances Data)

Upstream product

• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 108-12-3 isopentanoyl chloride 
• 104-94-9 4-methoxy-aniline 
• 14371-10-9 (E)-3-phenylpropenal 
• 139007-44-6 S-(2-pyridinyl) 3-methylbutanethioate 
• 80542-40-1 N-cinnamylidene-p-anisidine 
• 127055-08-7 α-(Phenylthio)isovaleryl chloride 
• 132377-47-0 (E)-(2R,3S)-2-Isopropyl-3-(4-methoxy-phenylamino)-5-phenyl-pent-4-enoic acid 

Downstream Products

• 103733-18-2 (3R,4S)-3-Isopropyl-4-((E)-styryl)-azetidin-2-one 

Relevant articles and documents

Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity

The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords β-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans β-lactams, while sterically non-requiring or chelating groups favour the formation of the cis-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.

MILD AND CONVENIENT ONE-POT SYNTHESIS OF β-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES

Treatment of 2-pyridylthioesters with triethylamine in the presence of titanium tetrachloride affords titanium enolates that add to imines to give β-lactams in fair to excellent yields with moderate to good stereoselectivity.

Asymmetric synthesis of β-lactams and the carbapenem antibiotic (+)-PS-5

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