Deoxygenation at the C3 position of D- and L-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives

Abstract

Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-β-D- and β-L-threo-pentofuranose (1,2-O-isopropylidene-β-D- and β-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)3 on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates.

Keywords: Arabinose; Chiral pool; Cordycepose; Deoxygenation; Stereoselective synthesis.