Bicyclic nucleosides; stereoselective dihydroxylation and 2'-deoxygenation.
A series of polyhydroxylated bicyclic nucleoside derivatives is approached applying stereoselective dihydroxylation reactions. Three out of four isomeric and protected products were obtained after the stereoselectivity of dihydroxylation has been completely inverted comparing a bicyclic nucleoside with a tricyclic furanose substrate. A corresponding 2'-deoxynucleoside derivative has been obtained after an optimized deoxygenation procedure.
Ravn
Jacob
J
Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Freitag
Morten
M
Nielsen
Poul
P
D006900:Hydroxylation; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
D009705:Nucleosides; D010100:Oxygen