Synthesis of tricycles based on 1,6-anhydro-beta-D-hexopyranoses fused with morpholine. 3,10,12-trioxa-6-azatricyclo[7.2.1.0(2,7)]dodecanes

摘要

The key step of the synthetic route was opening of the oxirane ring in 1,6: 3,4-dianhydro- 2-O-tosyl-beta-D-galactopyranose (1) with 2-chloroethanol to give 1,6-anhydro-4- O-(2-chloroethyl)-2-O-tosyl-beta-D-glucopyranose (2), which was converted in four steps into 4-O-(2-aminoethyl)-1,6: 2,3-dianhydro-beta-D-mannopyranose (6). The latter compound underwent intramolecular cyclisation to afford the fused morpholine derivative 3-amino-1,6- anhydro-3-deoxy-3-N,4-O-ethylene-beta-D-altropyranose (7) which gave the corresponding quaternary ammonium salt 11 by N-methylation. Acid cleavage of the 1,6- anhydro bond in 7 gave 3-acetamido-3-deoxy-3-N,4-O-ethylene-D-altropyranose (9). [References: 19]