252681-07-5

Basic information

• Product Name: (4S)-3,3-difluoro-4-phenylazetidin-2-one
• Synonyms: (4S)-3,3-difluoro-4-phenylazetidin-2-one
• CAS NO: 252681-07-5
• Molecular Weight: 183.157
• Mol File: 252681-07-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (4S)-3,3-difluoro-4-phenylazetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-3,3-difluoro-4-phenylazetidin-2-one(252681-07-5)
• EPA Substance Registry System: (4S)-3,3-difluoro-4-phenylazetidin-2-one(252681-07-5)

Safety Data

• Hazardous Substances Data: 252681-07-5(Hazardous Substances Data)

Upstream product

• 252681-06-4 (4S)-3,3-difluoro-4-phenyl-1-(1-phenylvinyl)azetidin-2-one 
• 31490-38-7 N-(4-methoxybenzyl)benzaldimine 
• 100-52-7 benzaldehyde 
• 252681-08-6 rac-3,3-difluoro-1-(4-methoxybenzyl)-4-phenylazetidin-2-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 252681-09-7 rac-3,3-difluoro-4-phenylazetidin-2-one 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 150884-50-7 benzaldehyde N-boc imine 
• 1277192-13-8 (S)-tert-butyl N-(2-(phenoxycarbonyl)-2,2-difluoro-1-phenylethyl)carbamate 
• 1277191-97-5 (S)-tert-butyl N-(2,2-difluoro-3-oxo-1,3-diphenylpropyl)carbamate 
• 109-73-9 N-butylamine 
• 75-31-0 isopropylamine 
• 78-81-9 isobutylamine 

Relevant articles and documents

Regio- and stereoselective lipase-catalysed acylation of methyl α-D-glycopyranosides with fluorinated β-lactams

Burkholderia cepacia lipase (lipase PS-D) catalysed acylation with 3,3-difluoro-4-phenyl-, -thiophen-3-yl- and -4-pyridylazetidin-2-ones was examined for the formation of N-Boc-protected 6-O-acylated sugar-β-amino acid conjugates from methyl α-D-galacto-, -gluco- and mannopyranosides and Boc2O. The 6-O-acylated glycopyranoside-β-amino acid conjugates were isolated and characterized. The low solubility of the gluco- and mannopyranosides and the high reactivity of the pyridylazetidinone restricted product formation. Activation of the β-lactam ring by the presence of fluorine substituents was shown to be necessary for the enzymatic acylation reaction. The (S)-enantiomers of the racemic β-lactam substrates reacted with the sugars. The lipase-catalysed diastereoselective ring-opening of aromatic and hetero-aromatic β-lactams was explored for the formation of β-amino acid conjugates of methyl α-D-glycopyranosides. Potential hydrolytic side-reactions were minimized by a suitable choice of solvent, lipase preparation and the use of molecular sieves.

Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis

The work describes fluorine-activated and N-Boc-activated β-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the β-lactam ring causes the ring to open in high enantioselectivity

Chemoenzymatic preparation of fluorine-substituted β-lactam enantiomers exploiting Burkholderia cepacia lipase

Both enantiomers of fluorinated and non-fluorinated 4-phenyl-2-azetidinones are prepared in high enantiopurities (ee 99%) by a chemoenzymatic method, using a double resolution technique to N-hydroxymethylated β-lactams in the presence of Burkholderia cepa