The synthesis of oligomers containing alternating -glycosyl α-amino acids and proteinogenic α-amino acids

C -Glycosyl amino acids are a group of C -glycosides in which a carbohydrate molecule is attached to the side chain or backbone of the amino acid via a C-C bond. Despite the numerous methods that have been developed for their synthesis, the C -glycosyl α-amino acids and their oligomers are relatively unexplored. In this work, we presented a protocol for the synthesis of oligomers containing alternating C -glycosyl α-amino acids and proteinogenic α-amino acids. The methodology is based on the modification of α-acyloxyamides obtained from the Passerini reaction using α- d -galactopyranose- and α- l -sorbofuranose-derived aldehydes as C -glycosyl donors. The protocol enabled the synthesis of homo- and heterochiral tetramers, and homo- and heterovalent tetramers in very good yields. C -Glycosyl α-amino acid in homo- and heterochiral, homo- and heterovalent oligomers.