Collect. Czech. Chem. Commun.
1998, 63, 813-825
https://doi.org/10.1135/cccc19980813
Preparation of 2,3-Dideoxy-2,3-epimino and 3,4-Dideoxy-3,4-epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses by Mitsunobu Reaction
Jiří Kroutila, Tomáš Trnkaa, Miloš Buděšínskýb and Miloslav Černýa
a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
Abstract
A series of new 2-, 3- and 4-benzylamino-2-, 3- and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses by treatment with benzylamine and converted into 2,3-(N-benzylepimino)-2,3-dideoxy- and 3,4-(N-benzylepimino)-3,4-dideoxy-β-D-hexopyranoses of the D-allo, D-galacto and D-talo configuration by Mitsunobu reaction. The structures of benzylamino and benzylimino derivatives were confirmed by 1H and 13C NMR spectra.
Keywords: Anhydrosugars; Oxiranes; Aziridines; Epimino derivatives; Aminosugars; Carbohydrates; NMR spectroscopy.
