(1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate

Abstract

Treatment of N-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysis, as well as FT-IR, NMR spectroscopic and HRMS analysis.

Keywords

• sialic acid
• N-acetylneuraminic acid
• 1,4 lactones
• γ-lactones
• polyhydroxylated compounds