Reaction of 3′,5′-di-O-acetyl-2′-deoxyinosine with the chlorinating agent PPh3–CCl4: synthesis of the 6-chloroderivative and of a new base linked dimer, useful intermediate to 15N-1-labelled 2′-deoxyinosine

Abstract

Treatment of 3′,5′-di-O-acetyl-2′-deoxyinosine 1 with PPh₃–CCl₄ in the presence of catalytic 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded 6-chloro-9-(2′-deoxy-3′,5′di-O-acetyl-β-D-ribofuranosyl)purine 3. Use of an excess of DBU gave the new dimeric bipurine 5(90%) which proved to be a useful intermediate for obtaining, in one step, [¹⁵N-1]-2′-deoxyinosine.