Nitrone in L-lyxose series:: cycloaddition way for the synthesis of new C-α-fucosides

Nitrone 3 analogue of 5-deoxy-L-Iyxose was derived from D-ribose. Its reduction with aqueous SO2 gave the corresponding 4-amino-sugar 2, a potent alpha-L-fucosidase inhibitor. 1,3-Dipolar cycloaddition of 3 with alkenes allowed the synthesis of acetohydroxamic acid and cthane-phosphonate derivatives. Hydroxy-ethane derivative 15 is a nanomolar alpha-L-fucosidase inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.