The nucleophilic substitution of the OTf group in 1a, b by amines and aminoalcohols opens a new route to N2-alkylated deoxyguanosines. Starting from 1 a,b, biologically relevant N2-deoxyguanosine adducts of carcinogenic alkylating agents are obtained, for example the ultimate carcinogenic (±)-anti-dihydrodiolepoxide of benzo[a]pyrene. TBDMS = tert-butyldimethylsilyl. a: R1 = p-nitrophenylethyl, b: R1 = allyl; Tf = CF3SO2.
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Steinbrecher et al. (1993) studied this question.
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