Conversion of glycosyl fluorides into C-glycosides using organoaluminum reagents. Stereospecific alkylation at C-6 of a pyranose sugar

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Abstract

Various furanosyl and pyranosyl fluorides react rapidly with alkyl, alkenyl, alkynyl, and aryl organoaluminum reagents at or below room temperature to form C-glycosides in 68-93% yields. Effective application of this procedure to a 6-fluoro 1,6-anhydroglucose derivative produced a chain-extended sugar stereospecifically. © 1985.

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Posner, G. H., & Haines, S. R. (1985). Conversion of glycosyl fluorides into C-glycosides using organoaluminum reagents. Stereospecific alkylation at C-6 of a pyranose sugar. Tetrahedron Letters, 26(15), 1823–1826. https://doi.org/10.1016/S0040-4039(00)94747-6

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