De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide.
A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective acylation were employed for the assembly of the L-rhamno-trisaccharide building block. The anthrose building block also required a palladium-catalyzed azide allylation and a triflate inversion to set the gluco-stereochemistry in addition to Luche reduction and dihydroxylation.
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Haibing
H
Guo
George A
GA
O'Doherty
D001408:Bacillus anthracis / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D009844:Oligosaccharides; D010165:Palladium