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Toward L-homo-DNA: stereoselective de novo synthesis of [beta]-L-erythro-hexopyranosyl nucleosides

Authors :
D'Alonzo, Daniele
Guaragna, Annalisa
Van Aerschot, Arthur
Herdewijn, Piet
Palumbo, Giovanni
Source :
Journal of Organic Chemistry. Oct 1, 2010, Vol. 75 Issue 19, 6402-6410
Publication Year :
2010

Abstract

A novel route is developed for 2' ,3' -dideoxy-[beta]-L-erythro-hexopyranosyl nucleosides equipped with a 1' -([N.sup.6]-benzolyadenin-9-yl) or a 1' -(thymin-1-yl) moiety. The synthesis of the enantiopure sugar moiety is performed by a de novo approach based on a domino reaction as the main step and N-glycosylation is analyzed by either nucleobase-transfer mechanism or in situ anomerization.

Details

Language :
English
ISSN :
00223263
Volume :
75
Issue :
19
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.240425238