Collect. Czech. Chem. Commun. 2007, 72, 1331-1349

Synthesis of Novel Carbocyclic Nucleosides and Pro-Tides Derived from 4-Oxatricyclo[,7]nonane-9-methanol

Hubert Hřebabecký*, Martin Dračínský and Antonín Holý

Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v. v. i., 166 10 Prague 6, Czech Republic


(1R*,2R*,3R*,6R*,7S*)-2-Amino-4-oxatricyclo[,7]nonane-9-methanol (9) was prepared from (1R*,2R*,3R*,4S*)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol by treatment with benzyl azidoformate followed by hydrogenolysis. The amine 9 was transformed to thymine and purine nucleoside analogues. The prepared analogues were converted to corresponding Pro-Tides by treatment with methyl N-[chloro(phenoxy)phosphoryl]-L-alaninate in the presence of 1-methylimidazole or tert-butylmagnesium chloride.

Keywords: Nucleosides; Purines; Pyrimidines; Pro-drugs; Pro-nucleotides; Phosphoramidates; Antiviral activity.

References: 26 live references.