Enantiopure synthesis of carbohydrates mediated by oxyselenenylation of 3,4-dihydro-2H-pyran

Abstract

Oxyselenenylation of 3,4-dihydro-2H-pyran with (S,S)-hydrobenzoin and subsequent stereoselective transformations afforded the enantiopure L- and D-arabinose while a disaccharide, 6-O-(β-D-arabinopyranosyl)-1,2∶3,4-di-O-isopropylidene-α-D-galactopyranose (13) was synthesized from 3,4-dihydro-2H-pyran by utilizing the same methodology.