title: De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.
abstract: [reaction: see text] A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed. Our approach relies on the iterative application of a palladium-catalyzed N-glycosylation, diastereoselective reduction, and reductive 1,3-transposition. This strategy is amenable to prepare various natural and unnatural hexopyranosyl nucleosides analogues.
authors.affiliation: Department of Chemistry, West Virginia University, Morgantown, 26506, USA.
authors.forename: Sanjeeva R
authors.initials: SR
authors.lastname: Guppi
authors.forename: Maoquan
authors.initials: M
authors.lastname: Zhou
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D002384:Catalysis; D006031:Glycosylation; D008958:Models, Molecular; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009705:Nucleosides; D010165:Palladium; D000241:Adenosine