Synthetic study on α(2→8)-linked oligosialic acid employing 1,5-lactamization as a key step

An attempt to synthesize α(2→8)-linked oligosialic acid utilizing a 1,5-lactamized sialyl acceptor is described. 1,5-Lactamization was experimentally proven to proceed only for α-sialoside, which was integrated into the synthetic cycle of oligosialic acid as a chemical sorting step to collect the desired α-sialoside and as a transformation step to produce a reactive sialyl acceptor for the next sialylation. Lactamized oligosialyl acceptors served as favorable coupling partners for sialylation, providing high stereoselectivities and high yields.