Synthesis and properties of C-aza-2-deoxy-L-lyxonucleosides †

Abstract

‘C-Aza-2-deoxy-L-lyxonucleosides’ in which a sugar ring oxygen is replaced with a nitrogen atom are synthesized from 2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranose via a sequential procedure of the addition of lithium salts of aromatic heterocycles, Swern oxidation and reductive aminocyclization. Their structures are determined mainly by X-ray crystallography and NMR measurements. Their bioassay is also described.

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