Collect. Czech. Chem. Commun. 2005, 70, 103-123

Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides

Hubert Hřebabecký*, Milena Masojídková and Antonín Holý

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


(1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-Amino-5-oxatricyclo[,7]nonane-3-methanols (16a and 17a) were prepared from 2-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2-methanol (10) in five easy steps. The amines 16a and 17a were used to construct 6-chloro-9H-purine 20 and 21, 2-amino-6-chloro-9H-purine 30 and 31, and 6-chloro-8-methyl-9H-purine analogues 34 and 35. Ammonolysis of these compounds led to 6-amino-9H-purine 22a and 23a, 2,6-diamino-9H-purine 32 and 33, and 6-amino-8-methyl-9H-purine derivatives of 5-oxatricyclo[,7]nonane-3-methanol 36 and 37. (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(Dimethylamino)-9H-purin-9-yl]-5-oxatricyclo[,7]nonane-3-methanols (22b and 23b), and (1R*,3R*,6R*,7S*,9S*)- and (1R*,3R*,6R*,7S*,9R*)-9-[6-(cyclopropylamino)-9H-purin-9-yl]-5-oxatricyclo[,7]nonane-3-methanols (22c and 23c) were prepared by aminolysis of 20 and 21.

Keywords: Amines; Oximes; Nucleosides; Carbocyclic nucleosides; Norbornanes; Purines; Carbanucleosides; LNA; Antivirals.

References: 26 live references.