99333-65-0

Upstream product

• 124918-14-5 1-benzyl-3β-[4(S)-phenyloxazolidin-2-one-3-yl]-4β-[2-(2-furyl)ethenyl]-azetidin-2-one 
• 2935-35-5 (S)-2-phenylglycine 
• 108493-65-8 (S)-ethyl (2-hydroxy-1-phenylethyl)carbamate 
• 99333-62-7 1-benzyl-3β-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4β-[2-(2-furyl)ethenyl]azetidin-2-one 
• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 99333-58-1 1-benzyl-4-(2-furyl)-1-azabuta-1,3-diene 
• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 99333-53-6 ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate 
• 123882-32-6 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid 

Downstream Products

• 110289-28-6 3β-t-butyloxycarbonylamino-4β-[2-(furan-2-yl)ethyl]azetidin-2-one 
• 124831-38-5 cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester 
• 124831-39-6 (6R,7S)-3-Chloro-7-[(R)-2-((E)-2-methoxycarbonyl-1-methyl-vinylamino)-2-phenyl-acetylamino]-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 119892-48-7 cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester 
• 124831-37-4 cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid 
• 119892-46-5 p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate 
• 76470-66-1 loracarbef 
• 123932-46-7 carbacephalosporin hydrochloride 
• 124831-36-3 N-[(2R,3S)-2-(2-Furan-2-yl-ethyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 
• 131533-82-9 [(3S,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 131533-88-5 [(3S,4R)-3-Benzyloxycarbonylamino-2-oxo-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 131533-89-6 3-[(2R,3S)-3-Benzyloxycarbonylamino-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid phenyl ester 
• 131533-85-2 [(3S,4R)-3-Benzoylamino-2-oxo-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 131533-92-1 [(3S,4R)-3-tert-Butoxycarbonylamino-2-oxo-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 

Relevant academic research and scientific papers

Process for Developing 3β-[4-(S)-Arylacetylamino-4β-(2-(2-furyl) ethyl]azetidin-2-one: A Carbacephem Key Intermediate

An optimized process for the stereospecific synthesis of carbacephem key intermediates 3β-[4-(S)-phenoxyacetylamino-4β-[2-(2-furyl)ethyl] azetidin-2-one (1) and 3β-[4-(S)-phenyl-acetylamino-4β-[2(2-furyl) ethyl)]azetidin-2-one] (2) is described. This repo

AN ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF (LY163892/KT3777)

An enantioselective synthesis of the new, orally absorbable, totally synthetic β-lactam antibiotic, loracarbef(LY163892/KT3777) is described.

Process and intermediates for β-lactam antibiotics

1-Benzyl (or substituted benzyl)-3β-[4(S)-aryloxazolidin-2-one-3-yl]-4β-(2-arylvinyl)azetidin-2-ones are provided via cycloaddition of a 4(S)-aryloxazolidin-2-one-3-ylacetyl halide and an imine formed with a benzylamine and a 3-arylacrolein, e.g. cinnamaldehyde. The azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-hydroxy-3-cephem-4-carboxylic acids and esters and to monocyclic β-lactam antibiotics.

The asymmetric synthesis of β-lactam antibiotics. I. Application of chiral oxazolidones in the Staudinger Reaction

The reactions of oxazolidone with N-benzylimines proceed with exceptional levels of asymmetric induction to form the cycloadducts. Subsequent dissolving metal reduction affords the homochiral β-lactam derivatives in good overall yield.