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Synthesis of Amino‐ L ‐Lyxose Phosphonates as Fucosyl‐Phosphate Mimics
Author(s) -
Chevrier Carine,
Le Nouën Didier,
Defoin Albert,
Tarnus Céline
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500990
Subject(s) - chemistry , phosphonate , pyrrolidine , nitrone , nucleophile , cycloaddition , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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)