An approach to a new class of selenosugars: a convenient synthesis of glycosyl isoselenocyanates

Abstract A new class of selenosugars—glycosyl isoselenocyanates—has been prepared via reaction of the corresponding glycosyl isocyanides with elemental Se under the catalytic influence of triethylamine. 2,3,4,5,6-Penta-O-acetyl-D-gluconyl isoselenocyanate was also prepared in moderate yield by reaction of 2,3,4,5,6-penta-O-acetyl-D-gluconyl chloride with potassium selenocyanate in anhydrous acetone. The isoselenocyanate structure is ascertained by physical (13C-NMR, IR) and chemical methods—formation of selenoureas, and radical induced fragmentation by reaction with tri-n-butyltin hydride via intermediate isocyanide, to 1,5-anhydro-D-hexitols.