Reaction of azide ion with 9-[2,3-anhydro-5-O-(p-tolylsulfonyl)-β- D -lyxofuranosyl]adenine

The reaction of 9-[2,3-anhydro-5-O-(p-tolylsulfonyl)-β-D-lyxofuranosyl]adenine (7) with sodium azide afforded 9-(2,5-anhydro-3-azido-3-deoxy-β-D-arabinofuranosyl)adenine (11) rather than the anticipated 5′-azido-2′,3′-anhydrolyxoside (8). Treatment of the azide 11 with sodium benzyl mercaptide resulted in formation of the Schiff base 15 via the 3′-amino-2′,5′-anhydroarabinoside (12). Compound 12 was also formed directly by hydrogenation of the azide 11.