61534-76-7

Upstream product

• 71698-17-4 3-Phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one 
• 35500-75-5 (1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one 

Downstream Products

• 64473-04-7 (2R,5R,6R)-benzyl 6-phenoxyacetamidopenam-2-carboxylate 
• 51989-07-2 (3S,5R,6R)-benzyl 6-phenoxyacetamidobisnorpenicillanate 
• 64473-03-6 (3R,5R,6R)-benzyl 6-phenoxyacetamidobisnorpenicillanate 
• 74740-85-5 2-[(2R,3R)-4-Oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-acrylic acid benzyl ester 
• 74732-83-5 2-Bromo-3-[(2R,3R)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-propionic acid benzyl ester 
• 74740-83-3 (3R,4R)-4-methoxycarbonylmethylthio-3-phenoxyacetamidoazetidin-2-one 
• 74732-84-6 2-Bromo-3-[(2R,3R)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-butyric acid benzyl ester 
• 83089-64-9 (3R,5R,6R)-t-butyl 2-(2-methoxyethylidene)-6-phenoxyacetamidopenam-3-carboxylate 
• 83089-63-8 (3S,5R,6R)-t-butyl 2-(2-methoxyethylidene)-6-phenoxyacetamidopenam-3-carboxylate 
• 78385-38-3 1-<(2R,3R)-4-oxo-3-phenoxyacetamidoazetidin-2-ylthio>-1-(1-benzyloxycarbonyl-1-bromomethyl)cyclopropane 
• 78385-39-4 (3S,5R,6R)-benzyl 6-phenoxyacetamidocyclopropanespiro-2-bisnorpenicillanate 
• 78385-39-4 (3R,5R,6R)-benzyl 6-phenoxyacetamidocyclopropanespiro-2-bisnorpenicillanate 
• 83089-73-0 (3R,5R,6R)-benzyl 6-phenoxyacetamido-2-isopropylidenepenam-3-carboxylate 
• 83089-72-9 (3S,5R,6R)-benzyl 6-phenoxyacetamido-2-isopropylidenepenam-3-carboxylate 

Relevant academic research and scientific papers

Generation, electrocyclic ring opening, and unprecedented conversion of a 3-acylaminoazetinone into cis-3,4-disubstituted azetidinones

An attempt to synthesize the nucleus of cefaclor by insertion of an appropriately functionalized rhodium carbene into a β-lactam N-H bond leads instead to attack at sulfur, followed by fragmentation into a four-membered thietanone and a four-membered 3-acylaminoazetinone. The azetinone undergoes electrocyclic ring opening, with a calculated half-life of 11 s at 40°C, to a trans-disubstituted vinyl isocyanate, but can be trapped by saturated, unsaturated allylic and benzylic alcohols to form 3,4-disubstituted azetidinones in which the cis- isomer predominates.

The Chemistry of 4-Mercaptoazetidin-2-ones. Part 1. Preparation and Properties of (3R,4R)-4-Mercapto-3-phenoxyacetamidoazetidin-2-one

(3R,4R)-4-Mercapto-3-phenoxyacetamidoazetidin-2-one (4) has been prepared in good yield from the penicillin V-derived thiazoline-azetidinone (1).Alkylation and acylation led exclusively to S-substituted azetidinones.Reaction with dimethyl acetylenedicarboxylate in hexamethylphosphoramide gave, in addition to the expected dimethoxycarbonylvinylthioazetidinone (15), the C-4-epimer (18).The latter probably arises via the intermediacy of the azetinone (16).

Certain 7-oxo-4-thio-2,6-diazabicyclo-3,2,0-hept-2-ene compounds

An intermediate represented by following formula for synthesizing 3-hydroxy-3-cephem compounds. STR1 wherein A and B each is a hydrogen or amino substituent; R is a hydrogen or thiol substituent; Hal is a halogen; X is a hydroxy or carboxy protecting grou