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 Original Research Arti

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 + 3ʹ 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.