Synthesis of [R-(R*,S*)]- and [S-(R*,R*)]-β-Hydroxy-3-(β-D-ribofuranosyl)- wybutines, the most probable alternatives for the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid

Article abstract of DOI:10.1016/S0040-4039(97)00253-0

The synthesis of the title compounds started with the Vilsmeier reaction of 3-[2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D- ribofuranosyl]wye (5b) and proceeded through the Wittig reaction with (R)-N-(methoxycarbonyl)-3-(triphenylphosphonio)alaninate (4), methylation with trimethylsilyldiazomethane, OsO₄ oxidation, cyclocondensation with triphosgene, and catalytic hydrogenolysis. Chromatographic separation of the resulting diastereomeric mixture and subsequent deprotection afforded the two desired nucleosides [[R-(R*,S*)]- and [S-(R*,R*)]-2b] for the first time.