Abstract
AbstractThe reductive metallation of the readily available peracetylated derivatives of methyl N‐acetylneuraminate 3a and 3b by samarium diiodide without any additive generates the corresponding anomeric samarium(III) organometallics. These intermediates react efficiently with carbonyl compounds under Barbier conditions, providing a fast synthesis of C‐ketosides. The α‐ and β‐acetates are equally effective, and excellent yields are obtained for coupling with cyclic ketones. The procedure has been conveniently applied to the synthesis of a C‐ketoside of N‐acetylneuraminic acid with an attached linker, ready to use as a building block in the elaboration of multivalent biological probes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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