Synthesis of flavonoid 2-deoxyglucosides via the Mitsunobu reaction

Abstract The Mitsunobu reaction of flavonoids and 3,4,6-tri- O -acetyl-2-deoxy- d -glucopyranose or 3,4,6-tri- O -benzyl-2-deoxy- d -glucopyranose is a very effective method for the stereoselective synthesis of flavonoid 2-deoxyglucosides. Since there is no C2 substituent on the sugar moieties, the observed α- or β-stereoselectivity was mainly controlled by the (acetyl or benzyl) protecting groups. Possible mechanistic insights are offered to explain the dual stereoselectivity.