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) / D’Alonzo, D.; Guaragna, Annalisa; A., Van Aerschot; P., Herdewijn; Palumbo, Giovanni. - 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)
D. D’Alonzo;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI
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.
