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De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-HNA) |
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| Authors: | Daniele D&rsquo Alonzo,Arthur Van Aerschot,Giovanni Palumbo |
| Affiliation: | a Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cinthia, 4 I-80126 Napoli, Italy b Katholieke Universiteit Leuven, Rega Institute for Medical Research, Minderbroederstraat 10, B-3000 Leuven, Belgium |
| Abstract: | A stereoselective and scalable route to 1,5-anhydrohexitol nucleoside analogues belonging to l-series as building blocks for l-HNA oligonucleotide synthesis has been efficiently tuned. Key to the successful outcome of our approach is the development of a DDQ-mediated domino reaction, which leads to the formation of an unsaturated 1,6-anhydrosugar derivative. Sugar elaborations and base insertion then enable to synthesize six-membered nucleosides. |
| Keywords: | 1,6-Anhydro-l-sugars Domino reactions Nucleosides analogues HNA Oligonucleotides |
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