198402-36-7

Upstream product

• 74503-07-4 allyl oxalyl chloride 
• 198402-35-6 (3S,4R)-4-{(1R,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-oxo-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 
• 198402-21-0 (1S,4aS,5S,8aR,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-3,3-di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one 
• 190973-61-6 (1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-2-one 
• 190973-56-9 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,2S,3S)-2-hydroxy-3-nitrooxy-cyclohexyl)-azetidin-2-one 
• 198402-34-5 (3S,4R)-4-{(1R,2S,3S)-3-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-2-hydroxy-cyclohexyl}-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 198402-04-9 {(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-5-yloxy}-acetic acid ethyl ester 
• 198402-14-1 {(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-5-yloxy}-acetic acid 
• 198402-06-1 [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester 
• 198402-05-0 {(1S,4aS,5S,8aR,8bR)-3,3-Di-tert-butyl-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-octahydro-4-oxa-2a-aza-3-sila-cyclobuta[a]naphthalen-5-yloxy}-acetic acid allyl ester 
• 198402-07-2 ((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyloxy)-acetic acid allyl ester 

Downstream Products

• 198402-37-8 (1S,5S,8aS,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester 

Relevant academic research and scientific papers

The synthesis of 4-aminocarbonylmethoxy trinems

The synthesis of 4-aminocarbonylmethoxy trinems was accomplished through Lewis acid catalysed opening of an epoxide intermediate with allyl glycolate, followed by deallylation, activation of the free acid via the 2-pyridyl thiolester and reaction with a series of trimethylsilylamines. An alternative route involving a rhodium-catalysed diazoacetate insertion was also successfully exploited.