61964-71-4

Upstream product

• 52709-42-9 benzylglyoxylate 
• 20781-20-8 2,4-Dimethoxybenzylamine 
• 40691-13-2 3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-2-one 

Downstream Products

• 121534-31-4 3-[(3S,4S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-4,5-diphenyl-3H-oxazol-2-one 
• 121534-31-4 3-[(3R,4R)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-4,5-diphenyl-3H-oxazol-2-one 
• 173105-04-9 (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic acid methyl ester 
• 161871-15-4 (3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-hydroxypropyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 161871-12-1 (3S,4S)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 161970-86-1 (3R,4R)-1-<1(R)-(methoxycarbonyl)-2(S)-O-<(tert-butyldimethylsilyl)oxy>propyl>-3-(2-oxo-4,5-diphenyl-1-oxazolinyl)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 
• 161970-87-2 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-azetidin-1-yl]-butyric acid methyl ester 

Relevant academic research and scientific papers

Enantioselective total syntheses of [6R,7R] and [6S,7S] tricyclic β-lactams

The reaction of Ox-glycyl chloride with a chiral imine derived from the combination of D-(R)-glyceraldehyde acetonide and protected D-threonine afforded optically active, highly functionalized cis-substituted β-lactams 11 and 12. These β-lactams provide versatile intermediates for the syntheses of biologically important carbacephalosporins, isooxacephems, and other multicyclic β-lactams. Desilylation and oxidation of 12 with Dess-Martin periodinane followed by intramolecular cyclization produced a novel tricyclic β-lactam 17 and a 1-(hydroxymethyl)-O-2-isocephem 18 with [6R,7R] absolute configuration. Removal of the Ox protecting group and acylation of 17 in a one-pot reaction followed by saponification furnished the target salt 24. Alternatively, reaction of phthaloylglycyl chloride with the chiral imine derived from the combination of L-(S)-glyceraldehyde acetonide and protected D-threonine gave only one enantiomeric azetidinone 27 in high yield. Further manipulation of 27 provided a new tricyclic β-lactam 39 with [6S,7S] absolute configuration which satisfies the stereochemistry typically required for antibacterial activity. This synthetic procedure provides a short, versatile and enantioselective method of preparing polycyclic β-lactams. Biological testing of these tricyclic β-lactams indicated that salt 39 has potential inhibitory activity against four typical strains of bacteria.

Substituted azetidinones

Substituted azetidine intermediates for preparing novel bicyclic β-lactam penicillin analogs which have antibacterial activity are disclosed.

Methods and intermediates for preparing cis-4-oxoazetidine intermediates

The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

7-Acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives and bactericidal compositions and use thereof

A new series of 7-acylamino-8-oxo-3-oxa-1-azabicyclo-[4.2.0]octane-2-carboxylic acid derivatives is described which compounds have antibacterial activity especially against certain Gram negative organisms.

Intermediates and methods for preparing 7-acylamino-8-oxo-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives

Intermediates and methods for preparing a new series of 7-acylamino-8-oxo-3-oxa-1-azabicyclo[4.2.0]-octane-2-carboxylic acid derivatives are described. The end product compounds have antibacterial activity especially against certain Gram negative organisms.

Cis-4-oxoazetidine intermediates and methods of preparing them

The stereospecific cycloaddition of nitrogen containing acetic acid halides or anhydrides with Schiff bases having a carbalkoxy group substituted on the methine carbon atom offers new intermediates and methods for preparing synthetic cephalosporin congeners having antibacterial activity.

8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives

Novel bicyclic β-lactams and intermediates useful in their preparation are disclosed. In particular, 7β-acyl-amino- and 7β-amino-8-oxo-4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acids are prepared. The acylated compounds are antibacterial agents.