90822-25-6

Upstream product

• 86978-81-6 Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 101765-69-9 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 101765-69-9 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 90822-24-5 (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester 
• 90776-58-2 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 
• 90776-58-2 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 

Downstream Products

• 90776-59-3 (4S,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-59-3 (4R,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 97033-04-0 (4S,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 93711-81-0 (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 258839-94-0 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-1-methyl-2-(7-pivaloylimidazo[5,1-b]-thiazol-2-yl)-1-carbapen-2-em-3-carboxylate 
• 258839-97-3 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-isobutyrylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-01-6 4-nitrobenzyl(1S,5R,6S)-2-(7-acetyl-5-methylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-10-7 4-nitrobenzyl(1S,5R,6S)-2-(7-ethanesulfonylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-18-5 4-Nitrobenzyl(1S,5R,6S)-2-(7-benzoylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxy-ethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-23-2 4-nitrobenzyl(1S,5R,6S)-2-(7-fluoroimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-26-5 4-nitrobenzyl(1S,5R,6S)-2-(7-acetylaminoacetylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-30-1 4-nitrobenzyl(1S,5R,6S)-2-(7-N-acetylaminomethylimidazo[5,1-b]thiazol-2-yl)-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-34-5 4-nitrobenzyl(1S,5R,6S)-2-[7-(N,N-dimethylcarbamoyl)acetylimidazo[5,1-b]thiazol-2-yl]-6-((1R)-1-hydroxyethyl)-1-methyl-1-carbapen-2-em-3-carboxylate 
• 258840-36-7 4-nitrobenzyl(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(7-methoxycarbonylimidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate 

Relevant academic research and scientific papers

Synthetic carbapenem antibiotics III. 1-Methyl thienamycin

Total syntheses of 1α- and 1β-methyl thienamycin are reported. 1β-Methyl thienamycin retains the antibacterial activity of thienamycin and is highly resistant to hydrolysis by HPD-1 enzyme.

Synthetic study of 1-substituted carbapenem antibiotics

Total synthesis of 1-substituted carbapenems is described. The key step is the reaction of acetoxyazetidinone with ketene silyl acetal.

SYNTHETIC CARBAPENEM ANTIBIOTICS I. 1-&β-METHYLCARBAPENEM

A total synthesis of a novel 1-β-methylcarbapenem antibiotic, (-)-(1R,5S,6S)-2-(2-N,N-dimethylamino-2-iminoethylthio)-6--1-methylcarbapen-2-em-3-carboxylic acid 1, is reported.Compound 1 is highly resistant to renal dipeptidase-I yet retains the excellent antibacterial activities of N-formimidoylthienamycin.