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Synlett 2000; 2000(9): 1366-1368
DOI: 10.1055/s-2000-7136
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Synthesis of Potent α-d-Mannosidase and α-l-Fucosidase Inhibitors: 4-Amino-4-deoxy-d-erythrose and 4-Amino-4,5-dideoxy-l-lyxose

Muriel Joubert* , Albert Defoin, Céline Tarnus, Jacques Streith
  • *École Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3, rue A. Werner, 688093 Mulhouse Cédex, France; Fax (33) (0)3 89 33 68 75; E-mail: A.Defoin@univ-mulhouse.fr
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Publication Date:
31 December 2000 (online)

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Amino-sugars 3a,b, analogues of l-fucose, and their sulfite adducts 11a,b were synthesised via asymmetric hetero Diels-Alder reaction and, for 3b, 11b, via methyl isomerisation of the intermediary oxazane-diol 7b. 4-Amino-d-erythrose sulfite adduct 11a is a potent α-d-mannosidase inhibitor, l-lyxose derivatives 3b, 11b are very active as α-l-fucosidase inhibitors.

hetero Diels-Alder - aminosugars - mannosidase inhibitors - fucosidase inhibitors