Collect. Czech. Chem. Commun. 1993, 58, 421-434
https://doi.org/10.1135/cccc19930421

Preparation of Purine 2'-Deoxy-5'-O-phosphonomethylnucleosides and 2'-Deoxy-3'-O-phosphonomethylnucleosides

Marcela Krečmerová, 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

Abstract

Sodium salt of 2'-deoxy-N6-dimethylaminomethylene-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (VIII) reacted with dibenzyl p-toluenesulfonyloxymethanephosphonate (Ia) to give dibenzyl ester of 2'-deoxy-N6-dimethylaminomethylene-5'-O-phosphonomethyl-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (XI) which after deprotection afforded the final 2'-deoxy-5'-O-phosphonomethyladenosine (XII). 2'-Deoxy-5'-O-hydroxymethanephosphonyladenosine (XIV) and 5'-O-benzyloxymethanephosphonyl-2'-deoxyadenosine (XIII) were isolated as a side product. The preparation of 2'-deoxy-5'-O-phosphonomethylguanosine (XVI) and protection of the starting nucleoside were analogous to those of compound XII. In the 2'-deoxy-3'-O-phosphonomethylnucleosides series, 2'-deoxy-3'-O-phosphonomethylcytidine (XXI) and 2'-deoxy-3'-O-phosphonomethyladenosine (XXVII) were prepared, using N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2'-deoxycytidine (XVIII) and 5'-O-tert-butyldiphenylsilyl-2'-deoxy-N6-dimethylaminomethyleneadenosine (XXIV), respectively, as starting compounds.