SYNTHESIS OF 2,3-UNSATURATED FURANIC HEX- AND PENT-ENOPYRANOSIDE EMPLOYING THE FERRIER REARRANGEMENT

Abstract

Glycosidation of various glycals with furanic alcohols in presence of catalytic amount of ceric(IV) ammonium nitrate under neutral condition or using Lewis acid-catalysed proceeds smoothly to afford the corresponding 2,3-unsaturated glycosides in good yields. In the hexose series predominantly α-D-anomers resulted while β-D-anomers are predominant in the pentose serie.



KEY WORDS: Ferrier rearrangement, Furanic alcohols, Glycosides, Ceric(IV) ammonium nitrate, Lewis acid catalyst


Bull. Chem. Soc. Ethiop. 2005, 19(2), 233-241.