CONVERSION OF GUANOSINE INTO 2-AMINOMETHYLINOSINE (2-HOMOGUANOSINE)

Abstract

2-Aminomethylinosine (1), a one-carbon extended homolog of an exocyclic amino group of guanosine, was synthesized from guanosine by the use of a newly developed protection and deprotection method. Introduction of a methoxy group into the 6-position of 2-benzenesulfonyl-purine riboside facilitated a nucleophilic substitution with cyanide to afford 2-cyano-6-methoxypurine riboside (11) which was subsequently hydrogenated and demethylated with trimethylsilyl iodide to afford 1.