Disiloxane-protected 2-deoxyribonolactone as an efficient precursor to 1,2-dideoxy-1-beta-aryl-D-ribofuranoses.
[formula: see text] Aryl C-nucleosides are analogues of natural nucleosides where the bases have been replaced with aromatic moieties. Work herein describes the highly stereoselective syntheses of non-hydrogen-bonding carbocyclic derivatives using a disiloxane-protected 2-deoxy-D-ribono-1,4-lactone as a stable and readily accessible starting material. Unlike the bis(TBDMS)-protected congener, this compound enables the use of sterically congested ortho-substituted aryllithium reagents in the initial addition reaction.
Wichai
U
U
Department of Chemistry and Coalition for Biomolecular Products, University of Alabama, Tuscaloosa 35487-0336, USA.
Woski
S A
SA
D005663:Furans / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013400:Sugar Acids / Q000737:chemistry*
D005663:Furans; D012821:Silanes; D013400:Sugar Acids; C059468:disiloxane; C056405:2,4,5-trihydroxypentanoic acid gamma-lactone