Synthesis and biological activities of octyl 2,3,4-tri-O-sulfo-α-L- fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-α-L-fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-α-L-fucopyranosyl-(1 → 3)-2,4-di-O-sulfo-β-L- fucopyranoside

Article abstract of DOI:10.1016/j.carres.2003.12.014

An efficient method for the regioselective 3-O-silylation of β-thiofucopyranoside was disclosed. Based on this discovery, we described a high-yielding strategy for the synthesis of the natural core structure of L-fucan and its fully sulfated derivative. The bioassay suggested that octyl 2,3,4-tri-O-sulfo-α-L-fucopyranosyl-(1→3)-2,4-di-O-sulfo-α-L- fucopyranosyl-(1→3)-2,4-di-O-sulfo-α-L-fucopyranosyl-(1→3)-2, 4-di-O-sulfo-β-L-fucopyranoside presented better antitumor activities than that of the free tetramer based on Sarcoma 180 cells and Lewis lung carcinoma model studies.