Catalytic effect of tetrabutylammonium fluoride in the preparation of secoribo-nucleosides

A general and rapid procedure is developed for the preparation of secoribo-nucleoside analogues. Bu₄NF has a marked effect on the condensation of guanine ( 5 ) with 2-(chloromethoxy)ethyl benzoate ( 2 ) or 1-halo-2-(chloromethoxy)ethanes 12 and 16 . Condensation and deprotection of the acyl protecting group and nucleophilic displacement of the halogen atoms to yield 9-(2-hydroxyethoxy)methyl] guanine ( 9 ) occurred in one step.