Alditol thiacrowns via a ring-closing metathesis of carbohydrate-derived α,ω-dithioallylethers

摘要: Abstract We report a newly developed synthesis of number alditol thiacrowns using an eco-friendly and versatile two-step strategy: the regioselective thioallyletherification polyhydroxylated followed by ring closing metathesis Grubbs second generation catalyst. This approach allows series target thiacrown products to be obtained in acceptable good yields, from corresponding α,ω-dithioallylether starting materials featuring either xylo, ribo, threo, erythro, d -manno or -gluco configurations. The per-O-acetylated -mannitol dithioallyether 10, easily on large scale this approach, was selected for evaluation as both antibacterial antioxidant. Although no activity observed bacterial strains investigated, compound 10 is shown antioxidant, able quench hydrogen peroxide stoichiometric fashion.