Collect. Czech. Chem. Commun.
2004, 69, 1818-1828
https://doi.org/10.1135/cccc20041818
Synthesis of Some 1,4-Oxazepanes Fused with 1,6-Anhydro-β-D-hexopyranoses. 3,11,13-Trioxa-7-azatricyclo[8.2.1.02,8]tridecane Derivatives
Tomáš Trteka, Miloslav Černýa, Tomáš Trnkaa, Miloš Buděšínskýb,* and Ivana Císařovác
a Department of Organic Chemistry, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
c Department of Inorganic Chemistry, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
Abstract
Some 1,4-oxazepanes based on 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:3,4-dianhydro-2-O-tosyl-β-D-galactopyranose (1). Cleavage of its oxirane ring with 3-chloropropanol gave 1,6-anhydro-4-O-(3-chloropropyl)-2-O-tosyl-β-D-glucopyranose (2), which was converted in three steps into 4-O-(3-aminopropyl)-1,6:2,3-dianhydro-β-D-mannopyranose (5). The latter compound underwent intramolecular cyclization to afford 3-amino-1,6-anhydro-3-deoxy-3-N,4-O-(propane-1,3-diyl)-β-D-altropyranose (6) that gave the corresponding quaternary ammonium salt 10 by N-methylation. Acid cleavage of the 1,6-anhydro bond in 7 gave the D-altrose derivative 3-acetamido-3-deoxy-3-N,4-O-(propane-1,3-diyl)-β-D-altropyranose (11).
Keywords: Carbohydrates; Heterocycles; 1,6-Anhydrosugars; 1,4-Oxazepanes; Amino sugars; Oxiranes; Epoxides; Cyclizations; X-Ray diffraction; NMR spectroscopy.
References: 12 live references.
