The Amadori rearrangement as key reaction for the synthesis of neoglycoconjugates Original Research Article

The Amadori rearrangement was introduced as a key step for the conjugation of carbohydrate moieties with suitable amines such as aliphatic amines and amino acid derivatives. The rearrangement products were further transformed into the corresponding 1-N,2-O cyclic carbamates employing triphosgene to obtain anomerically stable glycoconjugates. The reaction conditions were probed on a model substrate, 3,5-di-O-benzyl-α,β-d-glucofuranose and further applied to d-glycero-d-gulo-heptose, which gave ‘d-gluco-conjugates’ in the α-anomeric form exclusively in high isolated yields.