engleski

Synthesis, NMR and MS Study Of Novel N-Sulfonylated Purine Derivatives

Tosylation and mesylation of adenine (1) at room temperature give regioselectively N-9-sulfonylated purines 2 and 5. Excess of TsCl or MsCl at higher reaction temperatures leads to formation of unstable N-6, N-9-disulfonylated products 3 and 6, which easily transform into the corresponding N-6-monosulfonylated product 4. Two N-sulfonylated purine nucleoside derivatives 12 and 15 have also been prepared. 1D/2D NMR determined the site of sulfonylation and the spatial arrangement of the substituents. MS spectra showed unexpected rearrangement of protonated molecular ions that occurs upon the loss of SO2

synthesis; N9-sulfonyl; n6-sulfonyl; N6; N9-disulfonyl; purine derivatives; NMR study; MS study

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