Collect. Czech. Chem. Commun. 2002, 67, 1805-1819

Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening

Jiří Kroutila,*, Jindřich Karbanb, Tomáš Trnkaa, Miloš Buděšínskýc and Miloslav Černýa

a Department of Organic Chemistry, Charles University, 128 43 Prague 2, Czech Republic
b Institute of Chemical Processes Fundamentals, Academy of Sciences of the Czech Republic, 165 02 Prague 6, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The aziridine ring opening of N-tosylepimino carbohydrates 1-6 having D-allo, D-manno, D-galacto and D-talo configurations with benzyl alcohol, benzylamine and phenylmethanethiol afforded 2-, 3- and 4-O-benzyl-, benzylsulfanyl and benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-gluco, D-galacto and D-manno configurations 7-23 in 44-99% yields. Hexenopyranoses 24-26 were prepared from tosylepimino carbohydrates 1, 4 and 5 by intramolecular rearrangement of the aziridine ring.

Keywords: Carbohydrates; Ring opening reactions; Stereospecific synthesis; NMR spectroscopy; Aziridines; Amino sugars; Anhydro sugars; Nucleophilic additions.

References: 25 live references.