366785-58-2

Upstream product

• 366785-47-9 (3R,5S)-5-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 366785-56-0 (3R,5S)-5-((S)-1-Carboxy-2-phenyl-ethylcarbamoyl)-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 366785-43-5 (3R,5S)-Isoxazolidine-2,3,5-tricarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 542-92-7 cyclopenta-1,3-diene 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 366785-48-0 (3R,5S)-5-[(S)-1-((S)-1-tert-Butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 

Downstream Products

• 366785-59-3 (S)-2-({(3R,5S)-5-[(S)-1-((S)-1-tert-Butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-3-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 366785-49-1 (3R,5S)-3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-5-[(S)-1-((S)-1-tert-butoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-isoxazolidine-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Conformational study and enantioselective, regiospecific syntheses of novel aminoxy trans-proline analogues derived from an acylnitroso Diels-Alder cycloaddition

The cis/trans isomerization of the proline amide bond has many implications in biological processes. The conformations of representative acylnitroso-derived proline analogues derived from cyclopentadiene were shown to exist exclusively as the E or trans conformation in CD2Cl2. The energetically favored conformations were determined using COSMO self-consistent reaction field calculations at the B3LYP/6-31G* level of theory in addition to low temperature 1H NMR studies. The syntheses of the acylnitroso-derived peptides utilized two methods to selectively functionalize either of two chemically similar esters in the acylnitroso-derived amino acids. A novel transpeptidation of the amino acid that controlled the absolute stereochemistry in the acylnitroso Diels-Alder cycloaddition took advantage of an activated aminoxy amide linkage to control regiochemistry. Alternatively, an enantioselective and regiospecific enzymatic resolution of a racemic dimethyl ester provided a novel aminoxy acid.