A REGIOSELECTIVE SYNTHESIS OF ALKYL 2-(GUANIN-9-YL)ACETATES AS PNA BUILDING BLOCKS FROM 7-(4-NITROBENZYL)GUANINE DERIVATIVES

Collection of Czechoslovak Chemical Communications | January 1, 2005| | Copyright

Guanine derivatives substituted at N^sup 7^ with 4-R-benzyl groups (R = H, MeO, NO^sub 2^) have been evaluated in the regioselective N^sup 9^-alkylation of guanine. Given the capricious removal of (substituted) benzyl groups from guanine derivatives and pent-4-enoylation of guaninium hydrochloride, an improved alternative approach has been elaborated consisting in the pent-4-enoylation and per-O-acetylation of guanosine (8), 4-nitrobenzylation at N^sup 7^ followed by N-glycoside hydrolysis (10), N^sup 9^-alkylation (13) and deprotection with sodium dithionite to afford the peptide nucleic ...

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