title: Gram-scale synthesis of an armed colitose thioglycoside.
abstract: A concise gram-scale synthesis of protected colitose thioglycosides for use in bacterial carbohydrate antigen synthesis is described. The synthesis proceeds in six steps and 59-70% overall yield from commercially available l-fucose, making it the most efficient route reported to date. Key steps include regioselective installation of a thiocarbonate using catalytic dioctyltin dichloride (10 mol%) and a tris(trimethylsilyl)silane-mediated radical deoxygenation.
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Dina
authors.initials: D
authors.lastname: Lloyd
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
mesh_terms: D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D005643:Fucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003837:Deoxy Sugars; D012821:Silanes; D013865:Thioglycosides; C510691:tris(trimethylsilyl)silane; D005643:Fucose; C025141:colitose