Advantages of the Ns group in the reactions of N1-SO2R inosines with benzylamine and with 15NH3

The reactivity of N1-alkylsulfonyl- and N1-arylsulfonyl-2′,3′,5′-tri-O-acetylinosine with benzylamine and with 15NH3, regarding the attack on C2, has been shown to be in the order CF3SO2 (Tf) > 2,4-(NO2)2C6H3SO2 (DNs) ⩾ 4-NO2C6H4SO2 (pNs) ≈ C6F5SO2 (PFBs) > 2-NO2C6H4SO2 (Ns) ≫ CH3SO2 (Ms) > 4-CH3C6H4SO2 (Ts) > 2,4,6-(CH3)3C6H2SO2 (Mts). In spite of its intermediate reactivity, the Ns group is the most appropriate, since in this case the formation of by-products is minimised during the ring-opening and ring-closing steps of the process. Another advantage of the Ns group is thus disclosed.