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;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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/374298
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