Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf.
A wide variety of p-tolyl thioriboside donors are examined for O-ribosylations of primary and secondary alcohols. p-Tolylsulfenyl trifluoromethanesulfonate (p-TolSOTf) is very effective in promoting O-ribosylations with p-tolyl thioriboside; all reactions are completed within 1-15 min to provide the desired products in good yield with reliable alpha/beta selectivity. A wide range of functional groups are tolerated under these conditions. The described O-ribosylation conditions are very useful for the generation of ribosaminouridine library molecules in solution or on polymer support.
Kurosu
Michio
M
Department of Microbiology, Immunology, and Pathology, College of Veterinary Medicine and Biomedical Sciences, Colorado State University, 1682 Campus Delivery, Fort Collins, Colorado 80523-1682, USA. michio.kurosu@colostate.edu
Li
Kai
K
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D012266:Ribose / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013865:Thioglycosides / Q000138:chemical synthesis*
D000438:Alcohols; D007202:Indicators and Reagents; D008698:Mesylates; D011687:Purines; D011743:Pyrimidines; D013865:Thioglycosides; C543792:p-tolylsulfenyl trifluoromethanesulfonate; D012266:Ribose
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