• Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.

      Hansen, Steen Uldall; Baráth, Marek; Salameh, Bader A B; Pritchard, Robin G; Stimpson, William T; Gardiner, John M; Jayson, Gordon C; School of Chemistry and Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. gardiner@manchester.ac.uk (2009-10-15)
      L-ido cyanohydrin 3 was prepared from diacetone-D-glucose in four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-isopropylidine-protected L-ido nitrile (8), iduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamide) of heparin-related disaccharides.