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

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).