105344-46-5

Upstream product

• 105318-23-8 (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-carboxymethylazetidin-2-one 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 105318-31-8 (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-30-7 (3S,4S)-3-<(1R)-1-hydroxyethyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-04-5 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone 
• 105318-06-7 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-05-6 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-carboxyethyl>-2-azetidinone 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 158168-59-3 (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-phenylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 65750-59-6 2-(4-nitrobenzyloxycarbonylamino)ethanethiol 
• 108-98-5 thiophenol 
• 158168-62-8 (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfinyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 

Downstream Products

• 105318-41-0 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-phenylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant academic research and scientific papers

Practical synthesis of 1β-methylcarbapenem antibiotics: Side-chain substitution reaction of 2-arylsulfinyl and 2-arylsulfonyl carbapenems

The C-2 side-chain substitution reaction of a sulfoxide and a sulfone derived from a p-nitrobenzyl (1R,5S,6S)-6-[(1R)-1-(tert- butyldimethylsilyloxy)ethyl]-2-[2-(diethylcarbamoyl)phenylthio]-1- methylcarbapen-2-em-3-carboxylate with various mercaptans progressed smoothly in the presence of magnesium bromide. Bromomagnesium thiolate prepared from mercaptans proved to be especially effective for the substitution reaction and gave precursors of 1β-methylcarbapenem antibiotics in high yield.

Side chain substitution reaction of 2-arylsulfinyl and 2-arylsulfonyl intermediates for 1β-methylcarbapenems

Sulfoxide 5 and sulfone 6 derived from 1β-Methylcarbapenem 4 yielded the precursors of 1β-methylcarbapenems by MgBr2Et2O mediated C-2 side chain substitution reaction with functionalized mercaptans.

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.