TETRA-N-BUTYLAMMONIUM FLUORIDE AS A NOVEL REAGENT FOR THE PREPARATION OF ACYCLO-NUCLEOSIDES. THE SYNTHESIS OF 9- [(2-HYDROXYETHOXY) METHYL] ADENINE, BITAMYCIN.

The synthesis of the title compound, bitamycin, by means of BU4NF is described. This new antiviral drug was found to be one of the most powerful and least toxic substances for antiviral therapy in man. The physical and chemical behavior as well as the antiviral activities and clinical properties of this compound were found to be significantly different from that reported by Schaeffer, et al. Although the latter was claimed to have structure 1, we found it to possess structure 2. BU4NF was proved to be an effective reagent for the exclusive preparation of N(9)-alkylated products of purines. Condensation reactions and deprotection of the acyl-protecting groups to yield acyclo - nucleoside analogues were performed in a one step reaction.