De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.
[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.
Guppi
Sanjeeva R
SR
Department of Chemistry, West Virginia University, Morgantown, 26506, USA.
Zhou
Maoquan
M
O'Doherty
George A
GA
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
D009705:Nucleosides; D010165:Palladium; D000241:Adenosine