190973-56-9

Upstream product

• 67-56-1 methanol 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 

Downstream Products

• 198402-36-7 (1S,5S,8aS,8bR)-5-[2-(4-Benzenesulfonyl-piperazin-1-yl)-2-oxo-ethoxy]-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid allyl ester 
• 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 
• 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 
• 198402-10-7 (1S,5S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-5-(pyridin-2-ylsulfanylcarbonylmethoxy)-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester 
• 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 
• 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 
• 198402-09-4 (1S,5S,8aS,8bR)-5-Allyloxycarbonylmethoxy-1-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester 
• 198402-11-8 (1S,5S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-dimethylcarbamoylmethoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester 
• 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 
• 198402-12-9 (1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester 
• 198402-24-3 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1R,3S)-3-(2-morpholin-4-yl-2-oxo-ethoxy)-2-oxo-cyclohexyl]-azetidin-2-one 
• 198402-22-1 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1R,2S,3S)-2-hydroxy-3-(2-morpholin-4-yl-2-oxo-ethoxy)-cyclohexyl]-azetidin-2-one 
• 198402-08-3 ((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyloxy)-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 

Relevant academic research and scientific papers

Nitrate ester derivatives from epoxides using CAN: Efficient preparation of key intermediates in the synthesis of 4-alkoxytrinems

A regio and stereoselective opening reaction of epoxide with CAN (0.5 equivalents) in aprotic solvents is described. This novel reaction allowed the preparation of versatile nitrate estec derivatives as useful intermediates in the synthesis of trinems wid

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.