A novel simple pyrolytic approach towards anhydronucleosides

An interesting novel gas phase thermal intramolecular substitution reaction was discovered, which led to the conversion of the 2-β-d-N-glucosyl, 2-β-d-N-galactosyl and 2-β-d-N-ribosyl derivatives of 3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-ones into their corresponding 3,2′-anhydro-β-d-mannosyl, 3,2′-anhydro-β-d-talosyl and 3,2′-anhydro-β-d-arabinosyl derivatives. The structures of these new anhydroglycosyls were determined by NMR experiments and by X-ray crystallography.