Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-c-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-b-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding b-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.
beta-Peptoids: synthesis of a novel dimer having a fully extendedconformation
MARTELLI, Gianluca;MONSIGNORI, ANTONELLA;ORENA, MARIO;RINALDI, SAMUELE;
2012-01-01
Abstract
Chiral imines 1a,b, already synthesized in our laboratory, were converted in good yield by reduction into the corresponding N-benzyl-c-lactams 2a,b. Desilylation followed by oxidation of the hydroxymethyl functionality gave the N-benzyl-b-amino acids 5a,b in good yield and high purity. Starting from compound 6a, the corresponding b-peptoid dimer 8 was prepared, together with its derivatives 9 and 10, these latter displaying conformational restriction about the peptide bond, as evidenced by NMR data.File in questo prodotto:
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