Enantioselective Synthesis of Tetrafluoroethylene-Containing Monosaccharides†
A. James Boydell
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK, Fax: (+44) 23-8059-6805
Search for more papers by this authorVictoria Vinader Dr.
GlaxoSmithKline, Gunnels Wood Road, Stevenage SG1 2NY, UK
Search for more papers by this authorBruno Linclau Dr.
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK, Fax: (+44) 23-8059-6805
Search for more papers by this authorA. James Boydell
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK, Fax: (+44) 23-8059-6805
Search for more papers by this authorVictoria Vinader Dr.
GlaxoSmithKline, Gunnels Wood Road, Stevenage SG1 2NY, UK
Search for more papers by this authorBruno Linclau Dr.
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK, Fax: (+44) 23-8059-6805
Search for more papers by this authorWe thank GlaxoSmithKline for funding. We are grateful to Prof. R. J. Whitby and Dr. Martin Swarbrick for support. Abbreviations: AQN: anthraquinone; Bn: benzyl; DCC: dicyclohexylcarbodiimide; DHQ: dihydroquininyl; DMAP: 4-dimethylaminopyridine; PHAL: phthalazine; PYR: pyrimidine.
Graphical Abstract
A Sharpless asymmetric dihydroxylation of the commercially available building block 1 affords the common chiral intermediate 2 for the synthesis of the fluorinated monosaccharides 3–5 (Bn=benzyl).
Supporting Information
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