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An efficient route to 2'-homouridine (1), a new nucleoside analogue, is reported that is based on an ene reaction. This nucleoside has been incorporated into a dinucleoside monophosphate and hydrolytic studies on the dimer show that it does not behave like a ribonucleotide.
Functionalised 2 -C-branched nucleosides that contain either a carboxylic acid (2), a primary amide (3) or a primary hydroxyl (4) group have been prepared and their protection for oligonucleotide synthesis investigated. The 2 -C-3 -O-γ-butyrolactone (5) was also shown to be a useful intermediate for the preparation of these analogues.
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