167867-49-4

Upstream product

• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 119153-87-6 (C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅) 
• 145641-42-5 N-phenylalanine methyl ester 
• 145641-39-0 ((S)-1-Chlorosulfinylmethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 122818-32-0 (S)-2-<(tert-Butoxycarbonyl)amino>-3-phenylpropyl thioacetate 
• 126301-19-7 (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl methanesulfonate 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 145641-43-6 N-phenylalanine methyl ester 

Relevant academic research and scientific papers

Synthesis of Peptidosulfinamides and Peptidosulfonamides: Peptidomimetics Containing the Sulfinamide or Sulfonamide Transition-State Isostere

Synthetic routes are described toward the preparation of α- as well as β-substituted aminoethanesulfinyl chlorides, starting from either an aldehyde or from an amino acid derivative.The sulfinyl chlorides are used as building blocks for the preparation of homochiral α- or β-substituted sulfinamide and sulfonamide transition-state isosteres.The methodology has been applied to the synthesis of peptidosulfonamide peptidomimetics such as a hapten needed for the generation of antibodies and potential HIV protease inhibitors.In addition, the β-substituted aminoethanesulfinyl chlorides were used as building blocks for the preparation of a tetrapeptidosulfonamide, which can be considered as a biopolymer mimetic, employing a repetition of a cycle of three reactions: coupling of the sulfinyl chloride to the N-terminus of the growing peptidosulfonamide, oxidation to the sulfonamide, and deprotection of the N-terminus.