144574-07-2

Upstream product

• 300568-75-6 {(2R,3S)-2-[(1R,3S)-3-(Benzyloxycarbonyl-methyl-amino)-2-oxo-cyclohexyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 9H-fluoren-9-yl ester 
• 300568-77-8 5-(benzyloxycarbonyl-methyl-amino)-1-[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 9H-fluoren-9-yl ester 
• 300568-79-0 (1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 9H-fluoren-9-yl ester 
• 181228-87-5 (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S,2S,6R)-1-hydroxy-2-methylaminocyclohexyl-6-yl]azetidin-2-one 
• 185675-65-4 ((1S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohexyl)-methyl-carbamic acid benzyl ester 
• 300568-72-3 ((1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-hydroxy-cyclohexyl)-methyl-carbamic acid benzyl ester 
• 135297-03-9 (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 
• 60099-09-4 methanimidic acid phenylmethyl ester hydrochloride 
• 144574-08-3 (1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methylamino-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 

Relevant academic research and scientific papers

Highly diastereoselective synthesis of 4-N-methylformamidino trinem (GV129606), a potent antibacterial agent

In this paper a highly diastereoselective synthesis of 4-N-methylformamidino trinem 3 is reported. The route offers advantages compared to that previously used, i.e. the higher overall yield, the robustness, the avoidance of toxic reagents. Most of the compounds were isolated by precipitation, therefore reducing the number of chromatographic separations. The efficient conversion of 4-N-methylamino trinem 11 into GV129606 3, was obtained by a new methodology in which a scavenger resin was used. The route presented in this paper allowed the preparation of the material required for early development studies and demonstrates the versatility of cyclohexenyl azetidinone 12 in the synthesis of 4-substituted trinems. (C) 2000 Elsevier Science Ltd.

Synthesis and antibacterial activity of trinems bearing nitrogen derivatives at C(4)

Optimization of the antibacterial activity of 4-amino trinem, obtained through chemical modification of the basicity of the amino group at position 4, has led to the identification of a very interesting compound characterized by a broad spectrum of activi