New Chiral Nitrones in the Synthesis of Modified Nucleosides

Abstract New chiral nitrones 7 and 12, easily prepared from D-xylose by multistep synthetic routes, undergo regioselective 1,3-dipolar cycloadditions with N-vinylated bases (uracil, adenine) giving isoxazolidinyl nucleosides in good yields. Attack of the dipolarophile on the Z-configuration of the n...

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Bibliographic Details
Published in:Synlett 2002-07, Vol.2002 (7), p.1113-1117
Main Authors: Fischer, Róbert, Drucková, Alexandra, Fiera, Lubor, Rybár, Alfonz, Hametner, Christian, Cyra, MichaŠ K.
Format: Article
Language:English
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Summary:Abstract New chiral nitrones 7 and 12, easily prepared from D-xylose by multistep synthetic routes, undergo regioselective 1,3-dipolar cycloadditions with N-vinylated bases (uracil, adenine) giving isoxazolidinyl nucleosides in good yields. Attack of the dipolarophile on the Z-configuration of the nitrone through EXO and ENDO transition states from the SI face of nitrone (C-1′/C-3 ERYTHRO) affords C-3/C-5 CIS (EXO) and C-3/C-5 TRANS (ENDO) isoxazolidines as two major isomers.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2002-32579