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

Graphic Octyl 2,3-di- O-sulfo-α- l-fucopyranosyl-(1 → 3)-2- O-sulfo-α- l-fucopyranosyl-(1 → 4)-2,3-di- O-sulfo-α- l-fucopyranosyl-(1 → 3)-2- O-sulfo-α- l-fucopyranosyl-(1 → 4)-2,3-di- O-sulfo-β- l-fucopyranoside, a fucosyl pentasaccharide with a regular structure resembling the repeating unit of a natural sulfated fucan, was chemically synthesized using a convergent `2 + 3' strategy. Regioselective 3- O-silylation of β-thiofucopyranoside and AgOTf-catalyzed glycosylation of the protected glycosyl trichloroacetimidate facilitated a one-pot trisaccharide synthesis. The synthesized target compound showed good antitumor activity in vivo, and promising anticoagulant activity in vitro.