86998-35-8

Upstream product

• 76271-75-5 tert-butyldiphenylsilyloxyethanthioic acid 
• 86998-32-5 (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 86998-54-1 (R)-2-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2,5-dioxo-pyrrolidin-1-ylsulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester 
• 86998-44-9 (R)-2-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-methoxycarbonyl-ethanesulfinyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester 
• 86998-55-2 (R)-2-{(2R,3S)-2-Benzenesulfonylsulfanyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-3-enoic acid methyl ester 

Downstream Products

• 86998-38-1 (R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(tert-butyl-diphenyl-silanyloxy)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-3-enoic acid methyl ester 
• 86998-41-6 2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(tert-butyl-diphenyl-silanyloxy)-acetylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Desulphurative approaches to penem antibiotics. I. 4-acyldithioazetidin-2-ones via thermolysis of penicillin-derived sulphoxides

Thermolysis of penicillin-derived sulphoxides in the presence of thioacids offers a simple route to 4-acyldithioazetidin-2-ones, whose desulphurisation yields key intermediates for the synthesis of penem antibiotics.

DESULPHURATIVE APPROACHES TO PENEM ANTIBIOTICS. II. 4-ACYLDITHIOAZETIDIN-2-ONES FROM PENICILLIN DERIVED SULPHENIMIDES, THIOLSULPHONATES AND DISULPHIDES.

Displacement of different leaving groups from a number of 2-oxo-azetidin-4-ylthio derivatives with thioacids, followed by sulphur extrusion, provides a facile access to β-lactam thioesters and hence to penems.