Disiloxane-Protected 2-Deoxyribonolactone as an Efficient Precursor to 1,2-Dideoxy-1-β-aryl- d -ribofuranoses (original) (raw)

Organic Letters, 1999

Abstract

[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.

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