Thermolysis and Photolysis of Sugar Diazides

Article abstract of DOI:10.1246/cl.1994.1107

1,1-Diazido-2,3,4,5,6-penta-O-benzyl-D-glucose was refluxed in o-xylene under argon atmosphere to give 5-<(1'R,2'S,3'R-1',2',3',4'-tetrabenzyloxy)butyl>tetrazole in a high yield via an unpreceding rearrangement with one carbon shortening of sugar skeleton.In contrast its photolysis afforded two tetrazoles caused by the rearrangements without one carbon degradation: 5-<(1'S,2'R,3'R,4'R-1',2',3',4',5'-pentabenzyloxy)pentyl>tetrazole and 1-<1'R,2'S,3'R,4'R-1',2',3',4',5'-pentabenzyloxy)pentyl>tetrazole.