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

Graphic 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.