PREPARATION OF PURINE 2'-DEOXY-5'-O-PHOSPHONOMETHYLNUCLEOSIDES AND 2'-DEOXY-3'-O-PHOSPHONOMETHYLNUCLEOSIDES

Article abstract of DOI:10.1135/cccc19930421

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 side products.The preparation of 2'-deoxy-5'-O-phosphonomethylguanosine (XVI) and protection of the starting nucleoside were analogous to those for 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.