title: De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction.
abstract: The natural all d- and/or unnatural all l-1,4- and 1,6-oligosaccharides were synthesized from furan alcohols using a palladium-catalyzed glycosylation reaction. The 1,4- and 1,6-alpha-manno-disaccharides were achieved in seven total steps starting from chiral furan alcohols. Similarly, 1,4- and 1,6-alpha-manno-trisaccharides were also synthesized in nine total steps. Key to the overall efficiency of this process was the use of highly diastereoselective palladium-catalyzed glycosylations, reductions, and dihydroxylations.
authors.affiliation: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
authors.forename: Ravula Satheesh
authors.initials: RS
authors.lastname: Babu
authors.forename: Maoquan
authors.initials: M
authors.lastname: Zhou
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D002240:Carbohydrate Sequence; D002384:Catalysis; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D012210:Rhamnose / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D011714:Pyrans; D010165:Palladium; D012210:Rhamnose