Synthesis 2015; 47(13): 1893-1898
DOI: 10.1055/s-0034-1380571
paper
© Georg Thieme Verlag Stuttgart · New York

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

Joana Salta
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
,
Hans-Ulrich Reissig*
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany   Email: hans.reissig@chemie.fu-berlin.de
› Author Affiliations
Further Information

Publication History

Received: 24 February 2015

Accepted after revision: 23 March 2015

Publication Date:
29 April 2015 (eFirst)

Abstract

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.

Supporting Information

 
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