898831-83-9

Upstream product

• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 898831-82-8 (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester 
• 898831-81-7 (2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-hydroxybutyric acid ethyl ester 

Downstream Products

• 898831-84-0 (2S,3S)-2-(tert-butyldimethylsilanyloxy)-3-[(2,4-dimethoxybenzyl)ethoxycarbonylacetylamino]butyric acid ethyl ester 
• 898831-94-2 (6S,3aR)-5-(2,4-dimethoxybenzyl)-6-methyl-2,3,3a,5,6-pentahydro-5-azainden-4-one 
• 898831-88-4 (3S,6S)-3-allyl-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3,6-dihydro-1H-pyridin-2-one 
• 898831-96-4 (3S,6S)-1-(2,4-dimethoxybenzyl)-3-(3-hydroxypropyl)-4-iodo-6-methyl-3,6-dihydro-1H-pyridin-2-one 
• 1026532-72-8 (5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(2,4-dimethoxy-benzyl)-6-methyl-piperidine-2,4-dione 
• 898831-87-3 (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one 
• 898831-91-9 acetic acid {3-[(3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-2-oxo-1,2,3,6-tetrahydropyridin-3-yl]propyl} ester 
• 898831-92-0 (3S,6S)-3-[3-(tert-butyldimethylsilanyloxy)propyl]-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3,6-dihydro-1H-pyridin-2-one 
• 898831-77-1 (5S,6S)-1-(2,4-dimethoxybenzyl)-5-diphenylphosphoryloxy-4-iodo-6-methyl-5,6-dihydro-1H-pyridin-2-one 
• 898831-85-1 (5S,6S)-5-(tert-butyldimethylsilanyloxy)-1-(2,4-dimethoxybenzyl)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one 
• 898831-93-1 (3S,6S)-1-(2,4-dimethoxybenzyl)-4-iodo-6-methyl-3-[3-(2-nitrophenylselanyl)propyl]-3,6-dihydro-1H-pyridin-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of (Z)-alkene-containing proline dipeptide mimetics

In peptides and proteins, the peptide bond between an amino acid and proline exists as an equilibrium mixture of the cis-imide and trans-imide due to the low energy barrier in their interconversion. This feature greatly influences the structure and function of the proline-containing peptides and proteins. Therefore, restricting the amide bond with an (E)- or (Z)-alkene should provide a promising method for elucidating the structure-activity relationships of the peptide and the proteins. In this report, the regio-and stereoselective synthesis of cis-alanylproline (Ala-Pro) type (Z)-alkene dipeptide mimetic is described. The key steps of this synthesis are to introduce a C3 unit onto a γ-phosphoryloxy-α,β-unsaturated-(3-lactam with an organocopper-mediated anti-SN2′ reaction and subsequently construct a five-membered proline-like cyclic structure with an intramolecular Suzuki coupling reaction. Hydrolysis of the amide bond in the resulting bicyclic lactam yields the desired cis-Ala-Pro type (Z)-alkene dipeptide isostere. The presented synthetic methodology should be applicable to the general syntheses of other cis-aminoacylproline type (Z)-alkene dipeptide mimetics.