Collect. Czech. Chem. Commun. 2000, 65, 1126-1144

Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one

Zlatko Janeba*, Antonín Holý and Milena Masojídková

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


Reaction of 8-bromoadenine derivatives 2 with sodium acetate in acetic acid and cleavage of (S)-7-[(trityloxy)methyl]-7,8-dihydro[1,3]oxazolo[3,2-e]purin-4-amine (12) and diisopropyl (S)-{[(4-amino-8,9-dihydro-7H-[1,3]oxazino[3,2-e]purin-8-yl)oxy]methyl}phosphonate (13a) were used for the synthesis of the corresponding N9-substituted derivatives of 6-amino- 7H-purin-8(9H)-one 3a-3c and 7. Alkylation of 6-amino-7H-purin-8(9H)-one (3a) with diverse alkylation agents afforded the title N9-monosubstituted 3b, 3d and 7a and N7,N9-disub- stituted acyclic nucleoside and nucleotide analogs 6b, 6d and 8a.

Keywords: Purines; Acyclic analogs; Nucleosides; Nucleotides; Alkylation; Anhydro derivatives; Phosphonates; Bromination.

References: 31 live references.