Synthesis of Divalent Carbohydrate Mimetics by Reductive Amination with Enantiopure 1,2-Oxazines as Precursors

J. Salta, H.-U. Reissig

A direct approach to mono- and divalent carbohydrate mimetics starting from an enantiopure 1,2-oxazine derivative is described. After the Lewis acid induced rearrangement and subsequent reduction to provide the expected bicyclic 1,2-oxazine derivative as major component, a new tricyclic compound resulting from a different rearrangement pathway was isolated in small amounts. A smooth and optimized method for the hydrogenation of the bicyclic 1,2-oxazine derivative is presented, affording the desired aminopyran with d-idopyranose configuration. By reductive amination this aminopyran was connected with different aldehydes to furnish N-alkylated compounds. Reductive amination using 1,5-pentanedial resulted in the formation of a piperidine ring. With rigid aromatic dialdehydes the desired divalent compounds were obtained in good to excellent yields. Similar divalent carbohydrate mimetics were prepared from serinol.

Titel
Synthesis of Divalent Carbohydrate Mimetics by Reductive Amination with Enantiopure 1,2-Oxazines as Precursors
Verfasser
J. Salta, H.-U. Reissig
Kennung
10.1055/s-0034-1380571
Zitierweise
Synthesis 2015, 47(13), 1893-1898
Art
Text
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