158168-59-3

Upstream product

• 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 
• 146347-36-6 (R)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-(2-diethylcarbamoyl-phenyl) ester 
• 146347-56-0 2-[(E)-1-(tert-Butyl-dimethyl-silanyloxy)-propenylsulfanyl]-N,N-diethyl-benzamide 
• 81779-73-9 chloroxoacetic acid (4-nitrophenyl)methyl ester 
• 1026753-64-9 {(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-1-(2-diethylcarbamoyl-phenylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 
• 146347-76-4 S-(2-diethylcarbamoyl)phenyl thiopropionate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 49755-52-4 2,2'-disulfanediylbis(N,N-diethylbenzamide) 

Downstream Products

• 105344-46-5 (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 194983-50-1 (4R,5S,6S)-3-Benzylsulfanyl-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 158168-65-1 (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfonyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 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 

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.

A practical and stereocontrolled synthesis of a versatile 1β- methylcarbapenem intermediate

S[2(Dialkylaminocarbonyl)phenyl](2R)2[(3S,4S)3[(1R)1(tertbutyldimethylsilylox y)ethyl)]2oxo4azetidinyl]thiopropionate (11), useful intermediates for the synthesis of 1β-methylcarbapenems including 1β-methylthienamycin, were prepared in a highly stereoselective manner by the reaction of E-1-(tert- butyldimethyl-silyloxy)-1-[2-(dialkylaminocarbonyl)phenylthio]-1-propene (10) with commercially available (3S,4R)-3-[(1R)-1-(tert- butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (6) in the presence of zinc chloride catalyst. The diethylaminocarbonyl derivative (11b) was particularly convenient for practical production because of its highly crystalline nature.