Toward L-homo-DNA: stereoselective de novo synthesis of β-L-erythro-hexopyranosyl nucleosides.
A novel route to 2',3'-dideoxy-β-l-erythro-hexopyranosyl nucleosides equipped with a 1'-(N(6)-benzoyladenin-9-yl) or a 1'-(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.
D'Alonzo
Daniele
D
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, via Cinthia 4, I-80126 Napoli, Italy. dandalonzo@unina.it
Guaragna
Annalisa
A
Van Aerschot
Arthur
A
Herdewijn
Piet
P
Palumbo
Giovanni
G
D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009705:Nucleosides; D004247:DNA