161871-15-4

Upstream product

• 119599-96-1 methyl O-[tert-butyl(dimethyl)silyl]-D-threoninate 
• 161871-11-0 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-butyric acid methyl ester 
• 61964-71-4 ox-glycyl chloride 
• 40691-13-2 3-(carboxymethyl)-4,5-diphenyl-1-oxazolin-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 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 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 
• 173105-10-7 (1S,2R,3R,6S,7R)-7-Methyl-4-oxo-3-phenylacetylamino-8,10-dioxa-5-aza-tricyclo[5.2.1.0^2,5]decane-6-carboxylic 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.

Asymmetric Syntheses of β-Lactams and Determination of Their Absolute Configuration

Reactions of chiral imines derived from D-glyceraldehyde and threonine derivatives with Oxglycylchloride gave optically active cis-substituted β-lactams.The absolute configuration of key intermediates were determined by X-ray analysis and chemical degradation. - Key words: Asymmetric syntheses, D-glyceraldehyde, threonine, β-lactam, Staudinger reaction