De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction.
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.
Babu
Ravula Satheesh
RS
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Zhou
Maoquan
M
O'Doherty
George A
GA
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
D009844:Oligosaccharides; D011714:Pyrans; D010165:Palladium; D012210:Rhamnose