Collect. Czech. Chem. Commun. 1995, 60, 875-882

Synthesis of Acyclic Nucleotide Analogues Derived from 2-(Aminomethyl)adenine and 2-(Aminomethyl)hypoxanthine

Michal Hocek, Milena Masojídková and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


Synthesis of a series of 2-(aminomethyl)-9-(2-phosphonomethoxyalkyl)adenines VI and hypoxanthines VII is reported. The protected 2-(aminomethyl)adenine I was selectively alkylated with [bis(2-propoxy)phosphonylmethoxy]alkyl chlorides or tosylates II and the obtained 9-[bis(2-propoxy)phosphonylmethoxy]alkyl-2-(benzyloxycarbonyla minomethyl)adenines IV were oxodeaminated to give the corresponding hypoxanthine derivatives V. The intermediates IV and V were completely deprotected by treatment with iodotrimethylsilane under formation of the title compounds VI and VII.