Collect. Czech. Chem. Commun. 2004, 69, 1939-1954

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

Jindřich Karbana,*, Miloš Buděšínskýb and Jiří Kroutilc

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 and Nuclear Chemistry, Charles University, 128 40 Prague 2, Czech Republic


A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal trans azido tosylates. Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed.

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

References: 16 live references.