Asymmetric syntheses of the 2-deoxy-beta-oligosaccharide containing natural products via a palladium-catalyzed glycosylation

ORGN 74

Maoquan Zhou, maxo_zhou@yahoo.com and George A. O'Doherty, george.odoherty@mail.wvu.edu. C. Eugene Bennett Department of Chemistry, West Virginia University, Prospect Street, Morgantown, WV 26506
The synthesis of 2-deoxy-beta-glycosides has proven to be a challenging task due to the missing control element at the 2-position. An asymmetric synthesis of 2-deoxy-beta-monosaccharide has been developed and it is compatible to syntheses of the natural oligosaccharides digoxose and digitoxin. Our approach relies on the iterative application of a palladium catalyzed glycosylation, reductive 1,3-transpostion and diastereoselective dihydroxylations.