Synthesis of 9-β-D-Xylofuranosyl-6-mercaptopurine and 9-β-D-Xylofuranosylguanine 5'-Phosphate

Abstract

An attempt was made to synthesize 9-β-D-xylofuranosylguanine (VI) by condensation of N2, N9(or7)-diacetylguanine (I) and 1, 2, 3, 5-tetra-O-acetyl-D-xylofuranose (II) by a fusion method. However the main product obtained was 7-xylofuranosylguanine (III). Compound VI was successfully synthesized by deamination of 2-chloroadenine xyloside derivative (IV) with nitrous acid followed by amination with ammonia. VI was enzymati cally phosphorylated to give 9-β-D-xylofuranosylguanine 5'-phosphate. This Compound was found to have a flavoring activity. Catalytic hydrogenation of 2-chlorohypoxanthine derivative (V) with palladium-charcoal afforded hypoxanthine xyloside (IX), which, after acetylation, was chlorinated with phosphorus oxychloride to give the chloro compound (XII). This was converted by reaction with thiourea and subsequent ammoniacal treatment to 9-β-D-xylofuranosyl-6-mercaptopurine (XIII).