1254-56-4

Upstream product

• 113-98-4 penicillin G potassium salt 
• 100-51-6 benzyl alcohol 
• 36273-76-4 6ξ-(4-nitro-benzylideneamino)-penicillanic acid benzyl ester 
• 113-98-4 Penicillin G potassium 
• 100-39-0 benzyl bromide 
• 908094-04-2 phenyldiazomethane 
• 61-33-6 penicillin G 

Downstream Products

• 18598-31-7 benzylpenicillin 1,1-dioxide 
• 4052-54-4 Penicillin G 1-(s)-oxide 
• 106847-31-8 trans-(4S)-acetoxy-1-(1-benzyloxycarbonyl-2-methylpropenyl)-(3S)-phenylacetamidoazetidin-2-one 
• 1424272-93-4 C₁₇H₂₁N₂O₄S^(1-)*K⁽¹⁺⁾ 
• 1424272-92-3 cis-(4R)-t-butylthio-1-ethoxycarbonylmethyl-(3R)-phenylacetamidoazetidin-2-one 
• 74213-37-9 cis-(4R)-t-butylthio-(3R)-phenylacetamidoazetidin-2-one 
• 85027-68-5 (2S-trans)-N-<2-(acetyloxy)-4-oxo-3-azetidinyl>benzeneacetamide 
• 74481-22-4 benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate 
• 74481-09-7 benzyl 6β-allyl-6α-phenylselenopenicillanate 
• 74481-08-6 benzyl 6α-allyl-6β-phenylselenopenicillanate 
• 74481-12-2 benzyl (2S,5R,6S)-6-(phenylseleno)penicillanate 
• 15058-70-5 6-diazopenicillanic acid benzyl ester 
• 50269-19-7 C₂₃H₂₃N₃O₅S 
• 104430-19-5 (2R,4S)-2-((R)-Hydroxycarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

THE USE OF LIPOPHILIC BETA-LACTAM ANTIBIOTICS AND CARBOXYLATE ESTERS FOR THE TREATMENT OF BACTERIAL INFECTIONS WITHIN CITRUS AND OTHER PLANT SPECIES

Disclosed is method for converting a beta-lactam antibiotic into a “masked” beta-lactam antibiotic to permit it to cross the waxy cuticle of a plant and then subsequently unmasking the beta-lactam and converting it into an active beta-lactam antibiotic in

Studies on the design and synthesis of new monocyclic β-lactams containing substructures of penicillin G

The studies on design and synthesis of new monocyclic β-lactam esters 4(R/S)-(1′-methoxycarbonylpropyl-2′(R/S)-thio)-3(R)-phenylacetamidoazetidin-2-one (3a) and 4(R/S)-(1′-methoxycarbonyl-2′-methyl-propyl-2′-thio)-3(R)-phenylacetamidoazetidin-2-one (3b) were described. Compounds 3a and 3b were specifically designed to retain all penicillin substructures except the bicyclic system, which would be conceived by cleaving the C(3)-N(4) bond of penicillin G. Compounds 3a and 3b are of particular interest in the context of the structural elucidation of monocyclic β-lactams originated from penicillin. Key intermediates, β-mercapto esters 6a and 6b, were synthesized from conjugate acids 4a and 4b using three-step synthetic sequences, respectively, and 4(S)-acetoxy-3(S)-phenylacetamidoazetidin-2-one (7) was obtained from the degradation of penicillin G. Reactions of 6a and 6b with 7, thus obtained, provided the target compounds 3a and 3b, respectively.

Design and synthesis of new 4-alkylthio monocyclic β-lactams

New types of monocyclic β-lactams constitute an important class of compounds due to their unique structures and natures. Here, the design and synthesis of new 4-alkylthio monocyclic β-lactams 2a and 3a are reported. Significantly, compounds 2a and 3a, while keeping a monocyclic system, were designed to contain all of the substructures provided by the cleavage of C(2)-C(3) bond in penicillins. Efficient synthetic pathways for compounds 2a and 3a were established based on two different strategies. Compound 2a was synthesized from raw materials, using 4-acetoxyazetidin-2-one as a key intermediate, through a ten-step synthetic sequence in 3% overall yield. Compound 3a was synthesized from potassium salt of penicillin G (17), using the degraded product 20 as a key intermediate, through a six-step synthetic sequence in 11% overall yield. 4-Alkylthioazetidin- 2-one derivatives, introduced in this study, could serve as valuable intermediates for the development of new monocyclic β-lactams.