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.
De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-hna) / Palumbo, Giovanni; D'Alonzo, Daniele; Guaragna, Annalisa; A., Van Aerschot; P., Herdewijn. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 49:42(2008), pp. 6068-6070. [10.1016/j.tetlet.2008.07.159]
De novo approach to l-anhydrohexitol nucleosides as building blocks for the synthesis of l-hexitol nucleic acids (l-hna)
PALUMBO, GIOVANNI;D'ALONZO, DANIELE;
2008
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
