105370-87-4

Upstream product

• 97101-07-0 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one 
• 100-39-0 benzyl bromide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 96035-98-2 (3S,4S)-4-<(1S)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 

Downstream Products

• 161023-73-0 [(3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-1-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 105370-89-6 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-1-phenylthiocarbonylethyl>-2-azetidinone 

Relevant academic research and scientific papers

Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.