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[2,5-Dimethylfuran]-protected maleimides were placed at both internal positions and the 3′-end of oligonucleotides making use of solid-phase synthesis procedures. A new phosphoramidite derivative and a new solid support incorporating the protected maleimide moiety were prepared for this purpose. In all cases maleimide deprotection (retro-Diels–Alder reaction) followed by reaction with thiol-containing compounds afforded the target conjugate.