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Pure Appl. Chem., 2012, Vol. 84, No. 1, pp. 23-36

Published online 2011-12-08

Synthesis of novel carbohydrate mimetics via 1,2-oxazines

Léa Bouché and Hans-Ulrich Reissig*

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, D-14195 Berlin, Germany

Abstract: The combination of lithiated alkoxyallenes with carbohydrate-derived nitrones constitutes a flexible entry to highly functionalized enantiopure 1,2-oxazine derivatives. They can be used as precursors for acyclic and cyclic carbohydrate-like products such as amino sugar alcohols, azetidine and pyrrolidine derivatives. The Lewis acid-promoted rearrangement of 1,3-dioxolanyl-substituted 1,2-oxazines to bicyclic compounds allows an efficient route to novel amino pyran and oxepane derivatives. After subsequent transformations, new carbohydrate mimetics or “real” carbohydrates were obtained in good yield and often in a stereodivergent fashion. These compounds have already been employed for the preparation of unusual di- and trisaccharide derivatives. Several of the products prepared showed interesting biological activities, e.g., as L- and P-selectin inhibitors with IC50 values in the subnanomolar range.