A novel route to 20,30-dideoxy-β-L-erythro-hexopyranosyl nucleosides equipped with a 10-(N6-benzoyladenin-9-yl) or a 10-(thymin-1-yl) moiety has been developed. Synthesis of the enantiopure sugar moiety was carried out by a de novo approach based on a domino reaction as the key step.N-Glycosidation was explored via either nucleobase-transfer mechanism (B = T) or in situ anomerization (B = A or T), affording target nucleosides with high overall stereoselectivity.
Toward l-homo-DNA: stereoselective de novo synthesis of beta-l-erythro-hexopyranosyl nucleosides / D’Alonzo, D.; Guaragna, Annalisa; Van Aerschot, A.; Herdewijn, P.; Palumbo, Giovanni. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 75:19(2010), pp. 6402-6410. [10.1021/jo100691y]
Toward l-homo-DNA: stereoselective de novo synthesis of beta-l-erythro-hexopyranosyl nucleosides
D’Alonzo D.
;GUARAGNA, ANNALISA;PALUMBO, GIOVANNI
2010
Abstract
A novel route to 20,30-dideoxy-β-L-erythro-hexopyranosyl nucleosides equipped with a 10-(N6-benzoyladenin-9-yl) or a 10-(thymin-1-yl) moiety has been developed. Synthesis of the enantiopure sugar moiety was carried out by a de novo approach based on a domino reaction as the key step.N-Glycosidation was explored via either nucleobase-transfer mechanism (B = T) or in situ anomerization (B = A or T), affording target nucleosides with high overall stereoselectivity.| File | Dimensione | Formato | |
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