185675-65-4

Upstream product

• 501-53-1 benzyl chloroformate 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 
• 135297-03-9 (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsilyloxy)ethyl>-4-<(3'S)-cyclohex-1'-en-3'-yl>azetidin-2-one 
• 181228-87-5 (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S,2S,6R)-1-hydroxy-2-methylaminocyclohexyl-6-yl]azetidin-2-one 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 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 

Downstream Products

• 144574-07-2 GV129606 
• 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 
• 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 
• 185675-66-5 (1S,5S,8aS,8bR)-5-(Benzyloxycarbonyl-methyl-amino)-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 benzyl ester 
• 185675-67-6 (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 benzyl ester 
• 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 

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.

Determination of the absolute configuration of an unexpectedly stable N- silylated isomer isolated en route to the trinem antibiotic GV129606

The unexpected (3S,4R)-3-[(R)-1-(hydroxy)ethyl]-4-[(2'R,6'S)-1'-oxo-2'- (N-benzyloxy-N-methyl)aminocyclohexen-6'-yl]-1-(t-butyl- dimethylsilyl)azetidin-2-one was one of the main reaction products of the Lewis acid catalysed condensation of (3S,4R)-3-[(R)-

Synthesis and antibacterial activity of 4-ureido trinems

This article describes studies carried out on the synthesis and biological activity of 4-ureido trinems 1 obtained by the condensation of various isocyanates and the intermediate 6. Among others, 4-N-methyl-N'-alkyl ureido trinems showed a promising antimicrobial activity against Gram-negative bacteria.