129829-29-4

Upstream product

• 99333-53-6 ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-46-9 benzylamine 
• 99333-53-6 ((R)-2-Oxo-4-phenyl-oxazolidin-3-yl)-acetic acid ethyl ester 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 123882-32-6 2-[(R)-2-oxo-4-phenyloxazolidin-3-yl]acetic acid 
• 112674-71-2 (R)-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)acetyl chloride 
• 60293-41-6 N-((E)-3-phenylallylidene)benzylamine 
• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 123882-32-6 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid 
• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 99333-56-9 N-(3-phenylprop-2-enylidene)benzylamine 

Downstream Products

• 99333-63-8 (S)-3-((3S,4R)-1-Benzyl-2-oxo-4-phenethyl-azetidin-3-yl)-4-phenyl-oxazolidin-2-one 
• 110289-27-5 cis-1-benzyl-4-formyl-3-<(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl>-2-azetidinone 
• 129743-81-3 (S)-3-[(3R,4R)-1-Benzyl-3-((R)-1-hydroxy-butyl)-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 129743-82-4 (S)-3-[(3R,4R)-1-Benzyl-3-((R)-1-hydroxy-3-methyl-butyl)-2-oxo-4-((E)-styryl)-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 99333-70-7 (3S,4R)-3-Amino-4-phenethyl-azetidin-2-one 
• 99333-69-4 ((3S,4R)-2-Oxo-4-phenethyl-azetidin-3-yl)-carbamic acid tert-butyl ester 
• 99333-66-1 1-benzyl-3β-[(S)-4-phenyloxazolidin-2-one-3-yl]-4β-hydroxymethylazetidin-2-one 
• 129743-79-9 (3S,4R)-2,3-diamino-2-methyl-5-phenylpentanol 
• 129743-77-7 (3S,4R)-3-Amino-3-methyl-4-phenethyl-azetidin-2-one 
• 129743-87-9 (3S,4R,1'S)-3-(1'-hydroxy-2'-methyl)propyl-β-lactam 
• 129743-86-8 (3S,4R)-4-Phenethyl-3-{[1-phenyl-meth-(E)-ylidene]-amino}-azetidin-2-one 
• 129743-88-0 [(3R,4R)-3-((S)-1-Hydroxy-2-methyl-propyl)-2-oxo-4-phenethyl-azetidin-3-yl]-carbamic acid ethyl ester 
• 129743-84-6 [(3R,4R)-3-((R)-1-Hydroxy-2-methyl-propyl)-2-oxo-4-phenethyl-azetidin-3-yl]-carbamic acid phenethyl ester 
• 129743-78-8 (2S,3R)-2,3-diamino-2-methyl-5-phenylpentanoic acid dihydrochloride 

Relevant academic research and scientific papers

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.

7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof

7β-Acylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylic acid antibiotic compounds, esters and salts thereof, and the corresponding 7-amino and protected 7-amino 1-carbacephalosporins are provided. The 3-trifluoromethylsulfonyloxy-substituted 1-carbacephalosporins also are useful in a process for preparing 3-halo-1-carbacephalosporins which comprises reacting a 3-triflate ester with a lithium halide in an aprotic polar solvent.

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.