Facile Synthesis of 3′-C-Branched 1,5-Anhydrohexitol Nucleosides

Abstract

The 3′-β-C-branched anhydrohexitol nucleosides have been conveniently synthesised starting from commercially available D-ribose following the reaction sequence: (i) conversion of protected pentofuranose sugar to the corresponding hexopyranosyl nitrosugar (ii) addition of the conjugate base of nitrosugar to formaldehyde to obtain C-branched nitro sugar (iii) removal of nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to build up the nucleobase.