Catalytic oxidation-phosphorylation of glycals: rate acceleration and enhancement of selectivity with added nitrogen ligands in common organic solvents.
The first general catalytic oxidation of glycals has been developed to afford useful glycosyl phosphates in high yield and selectivity in a domino process with the use of catalytic methyltrioxorhenium, urea hydrogen peroxide, stoichiometric dibutyl phosphate as nucleophile, and a substoichiometric amount of nitrogen ligands, such as pyridine or imidazole, in organic solvents. [Structure: see text]
Soldaini
Gianluca
G
Dipartimento di Chimica Organica Ugo Schiff, Polo Scientifico, Università di Firenze, ICCOM C.N.R., via della Lastruccia 13, I-50019 Sesto Fiorentino, Florence, Italy.
Cardona
Francesca
F
Goti
Andrea
A
D002236:Carbohydrate Conformation; D002384:Catalysis; D006001:Glycoconjugates / Q000138:chemical synthesis; D007700:Kinetics; D008024:Ligands; D009005:Monosaccharides / Q000138:chemical synthesis*; D009584:Nitrogen; D009844:Oligosaccharides / Q000138:chemical synthesis; D009930:Organic Chemicals; D010084:Oxidation-Reduction; D010766:Phosphorylation; D012997:Solvents
D006001:Glycoconjugates; D008024:Ligands; D009005:Monosaccharides; D009844:Oligosaccharides; D009930:Organic Chemicals; D012997:Solvents; D009584:Nitrogen