34104-19-3

Upstream product

• 56526-47-7 (S)-2-((1S)-3-benzyl-7-oxo-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-(Ξ)-methanesulfinyl-3-methyl-butyric acid methyl ester 
• 49841-84-1 (S)-2-((1S)-3-benzyl-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-mercapto-3-methyl-butyric acid methyl ester 
• 56526-46-6 methyl (2S)-2-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methyl-3-methylthiobutanoate 
• 79434-35-8 methyl (2R)-2-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-3-enoate 
• 79386-25-7 methyl (2R)-2-<(3S,4S)-4-(benzothiazol-2-ylthio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-3-enoate 
• 56553-17-4 (S)-2-((1S)-3-benzyl-7-oxo-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-mercapto-3-methyl-butyric acid methyl ester; mercury(II) salt (2:1) 
• 67144-72-3 (2R)-<(3S,4R)-4-(benzothiazol-2-yldithio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-3-enoic acid 
• 4052-54-4 Penicillin G 1-(s)-oxide 
• 79386-27-9 (1S,5R)-3-phenylmethyl-6-<(1R)-1-carboxy-2-methylprop-2-enyl>-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one 
• 62284-24-6 methyl (2R)-<(3S,4R)-4-(benzothiazol-2-yldithio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-3-enoate 
• 38015-65-5 2-((R)-2-Chloro-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester 
• 653-89-4 penicillin G methyl ester 

Downstream Products

• 78115-02-3 (3S)-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamido-2-azetidinone 
• 121054-11-3 methyl 3-methyl-2-<(3S,4S)-2-oxo-3-phenylacetamido-4-pyruvoyloxyazetidin-1-yl>but-2-enoate 
• 79386-26-8 methyl 2-<(3S)-4-(benzothiazol-2-ylthio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-2-enoate 
• 105601-84-1 (3R,4R)-4-<(1-methyl-1H-tetrazol-5-yl)thio>-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamido-2-azetidinone 
• 105661-88-9 (3R,4S)-4-<(1-methyl-1H-tetrazol-5-yl)thio>-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamido-2-azetidinone 
• 71840-43-2 methyl 2-(2,4-dioxo-3-phenylacatamidoazetidin-1-yl)-3-methylbut-2-enoate 
• 78115-03-4 methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate 
• 80543-45-9 (S)-3-[[(phenylmethyl)carbonyl]amino]-2-azetidinone 
• 113641-80-8 3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethyl-4,5-dihydropyrazole-3-carboxylate 

Relevant academic research and scientific papers

STUDIES RELATED TO PENICILLINS. PART 26. CONVERSION OF POTASSIUM BENZYLPENICLLINATE INTO 1-SUBSTITUTED DERIVATIVES OF 3-PHENYL-ACETAMIDOAZETIDINE-2,4-DIONE

A new method for the synthesis of azetidine-2,4-diones, involving a Norrish Type II photoreaction of 4-pyruvoylazetidin-2-ones, has been devised.The process features in strategies in which potassium benzylpenicillinate (17a) is converted into 1-substitute

Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-sulfonic acid derivatives

Sulfazecin is a monocyclic β-lactam antibiotic isolated from strain G-6302, Pseudomonas acidophila. As a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-2-azetidinone was synthesized from penicillins, and various new compounds were s

Studies Related to β-Lactam Antibiotics. Part 7. Facile Formation of Oxazolinoazetidinones from Benzothiazolyldithioazetidinones and Related Reactions

4β-(Benzothiazol-2-yldithio)azetidin-2-one (2a), derived from penicillin G sulphoxide ester (1a), is converted competitively into the oxazolinoazetidinone (3a) and 4α-(benzothiazol-2-ylthio)azetidinone (4a) upon treatment with triphenylphosphine at room t

Studies Related to Penicillins. Part 19. Alkylations of (3R)-3-hept-2-en-6-yl>-4,4-dimethylthietan-2-one

The title compound (7a) unergoes epimerisation at position 3 of the thietanone ring in the presence of triethylamine; the equilibrium ratio of the starting material and its epimer (9a) is ca. 1.5 : 1.Methylation of the compounds (7a) or (9a) also occurs at position 3 of the thietanone ring, in the presence of sodium hydride-methyl iodide; a ca. 1 : 1 mixture of the (3R)-3-methylthietanone (7b) and the (3S)-3-methylthietanone (9b) is produced when tetrahydrofuran is used as the solvent whereas a ca. 2.5 : 1 mixture of the compounds (7b) and (9b) is formed when NN-dimethylformamide is employed.With potassium t-butoxide-t-butyl bromoacetate in NN-dimethylformamide, the thietanone (7a) affords a ca. 6 : 1 mixture of the (3R)-3-t-butyloxycarbonylmethylthietanone (7c) and its (3S)-isomer (9c).Only the (3R)-3-allylthietanone (7d) is formed when the thietanone (7a) is treated with potassium t-butoxide-allyl iodide in NN-dimethylformamide.Attempts to hydroxymethylate the thietanone (7a), by using potassium t-butoxide-formaldehyde, were thwarted by further reactions of the hydroxymethyl derivative (7e) or (9d), resulting in the formation of a mixture of 7-(α-mercapto-α-methylethyl)-3-phenylacetamido-1-aza-5,9-dioxabicyclodec-2-ene-4,8-dione (16a) and 11,11-dimethyl-5-phenylacetamido-3,9-dioxa-12-thia-7-azatricyclo1,7>dodecane-4,10-dione (20).

2,2-Dimethyl-3R-carboxy-6S-amino-1-oxa-4-aza-5R-bicyclo-[3,2,0]heptan-7-one

The title compound is produced by chemical synthesis and, if desired, converted as by N-phenylacetylation to a new β-lactam antibiotic such as oxapenicillin G.