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De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-HNA)
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-  smallcaps"  >l-sugars   Domino reactions   Nucleosides analogues   HNA   Oligonucleotides
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