Synthesis of Amino‐ L ‐Lyxose Phosphonates as Fucosyl‐Phosphate Mimics

Some reactions of nitrone 4 are described, namely the nucleophilic addition of dialkyl phosphites, HOP(OR) 2 , 5a – c or of diethyl methylphosphonate 8 and the dipolar [2+3] cycloaddition of vinylphosphonate 11 . Chemical transformations led to 4‐amino‐ L ‐fucose derivatives bearing a phosphonate group in the 1α position linked to the pyrrolidine ring through a chain of 0–2 carbon atoms. The target compounds proved to be good‐to‐excellent α‐ L ‐fucosidase inhibitors. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)