Collect. Czech. Chem. Commun. 2001, 66, 799-819

Synthesis and NMR Spectra of 1,6-Anhydro-2,3-dideoxy-2,3-epimino- and 1,6-Anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses

Jindřich Karbana,*, Miloš Buděšínskýb, Miloslav Černýc and Tomáš Trnkac

a Institute of Chemical Process Fundamentals, Academy of Sciences of the Czech Republic, 165 02 Prague 6, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
c Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic


A complete series of 2,3-dideoxy-2,3-epimino- and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by 1H and 13C NMR spectra.

Keywords: Carbohydrates; Aminosugars; Anhydrosugars; 1,6-Anhydro-β-D-hexopyranoses; Azides; Aziridines; Reductions; NMR spectroscopy.

References: 28 live references.