Investigations into the synthesis of amine-linked neodisaccharides

Six tail-to-tail amine-linked neodisaccharides were synthesised as potential glycomimetics. Primary–primary linked compounds were synthesised using Mitsunobu chemistry with glucose-6-sulfonamides as nucleophiles and primary carbohydrate alcohols as electrophiles. Primary–secondary linked compounds were synthesised by epoxide ring opening with carbohydrate 6-amines. Deprotection of all neodisaccharides was carried out using dissolving metal reduction.