Synthesis of analogues of nucleotides with all-carbon backbones: synthesis of N-protected C-linked dinucleotides

Abstract

Oxidative cleavage of the protected 3′-propenyl-3′-deoxythymidine 28 using osmium tetraoxide and sodium periodate gives the aldehyde 29 which is converted via the acid 30 and imidazolide 31 into the stabilized ylide 32. This is condensed with the thymidine derived aldehyde hydrate 24 to give the dinucleotide analogue 34. Hydrogenation and desilylation give the saturated dinucleotide analogues 36 and 37.