One-step synthesis of N-protected glycosylamines from sugar hemiacetals.
Protected pentofuranose, hexofuranose and hexopyranose hemiacetals were found to react efficiently with amines carrying a deactivating group (alkoxycarbonyl, tosyl or phosphoryl group) in the presence of a Lewis acid to give the corresponding, stable glycosylamines. Such glycosylamine derivatives are useful substrates for further elaboration into nitrogen-containing natural products and carbohydrate mimetics.
Liautard
Virginie
V
Institut de Chimie Organique et Analytique, University of Orléans, CNRS-UMR 6005, Rue de Chartres, F-45067 Orléans, France.
Pillard
Christelle
C
Desvergnes
Valérie
V
Martin
Olivier R
OR
D000080:Acetals / Q000737:chemistry*; D000606:Amino Sugars / Q000138:chemical synthesis*
D000080:Acetals; D000606:Amino Sugars