title: First gram-scale synthesis of a heparin-related dodecasaccharide.
abstract: The first example of a gram-scale synthesis of a structurally defined, heparin-related dodecasaccharide is reported. An iterative 14-step process using an iduronate donor disaccharide delivers >1g quantities of the dodecasaccharide sequence [GlcNS-IdoA2S](6)-OMe in 15% overall yield from the reducing terminal disaccharide, a 2 orders of magnitude increase in scale for access to synthetic heparanoid dodecasaccharide mimetics. The synthesis also delivers multigram amounts of the protected oligosaccharides from tetra- through to dodecasaccharide.
authors.affiliation: Manchester Institute of Biotechnology, School of Chemistry, Faculty of EPS, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK.
authors.forename: Steen U
authors.initials: SU
authors.lastname: Hansen
authors.forename: Gavin J
authors.initials: GJ
authors.lastname: Miller
authors.forename: Gordon C
authors.initials: GC
authors.lastname: Jayson
authors.forename: John M
authors.initials: JM
authors.lastname: Gardiner
mesh_terms: D006493:Heparin / Q000737:chemistry*; D007067:Iduronic Acid / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D009844:Oligosaccharides; D007067:Iduronic Acid; D006493:Heparin