Fusobacterium nucleatum, a colorectal-cancer-associated
oncomicrobe, can trigger or accelerate numerous pathologies. We report
the first synthesis of a conjugation-ready disaccharide containing
six amino groups from F. nucleatum ATCC 23726 O-antigen.
Rare 2,3-diamido-d-glucuronic acid amide and 2-acetamido-4-amino-d-fucose were synthesized from d-glucosamine through
configuration inversion, nucleophilic substitution, C6 oxidation,
and C6 deoxygenation. A judicious choice of protecting groups and
reaction conditions enabled the selective installation of N-acetyl, N-propanoyl, N-formyl, and carboxamido groups.