title: Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf.
abstract: 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.
authors.affiliation: 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
authors.forename: Michio
authors.initials: M
authors.lastname: Kurosu
authors.forename: Kai
authors.initials: K
authors.lastname: Li
mesh_terms: 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*
chemical_list: D000438:Alcohols; D007202:Indicators and Reagents; D008698:Mesylates; D011687:Purines; D011743:Pyrimidines; D013865:Thioglycosides; C543792:p-tolylsulfenyl trifluoromethanesulfonate; D012266:Ribose
references.citation: Curr Top Med Chem. 2005;5(13):1221-36
references.pmid: 16305528
references.citation: Bioorg Med Chem Lett. 2003 Sep 1;13(17):2833-6
references.pmid: 14611839
references.citation: Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5221-4
references.pmid: 15455432
references.citation: Chem Rev. 2000 Dec 13;100(12):4319-48
references.pmid: 11749350
references.citation: J Am Chem Soc. 2007 Aug 15;129(32):9885-901
references.pmid: 17655235
references.citation: Carbohydr Res. 1990 Jul 15;202:225-38
references.pmid: 2171766
references.citation: Adv Carbohydr Chem Biochem. 1997;52:179-205
references.pmid: 9218334
references.citation: Org Lett. 2007 Mar 15;9(6):1141-4
references.pmid: 17311394
references.citation: Glycobiology. 2001 Mar;11(3):25R-36R
references.pmid: 11320055
references.citation: Bioorg Med Chem Lett. 2001 Feb 26;11(4):529-31
references.pmid: 11229763
references.citation: Org Biomol Chem. 2006 Apr 7;4(7):1195-201
references.pmid: 16557303
references.citation: Heterocycles. 2010 Jan 1;80(1):115-123
references.pmid: 23239901
references.citation: Bioorg Med Chem. 2007 Aug 15;15(16):5629-50
references.pmid: 17544276
references.citation: Angew Chem Int Ed Engl. 2005 Mar 11;44(12):1854-6
references.pmid: 15723431
references.citation: Tetrahedron Lett. 2008 Feb 25;49(9):1542-1545
references.pmid: 18438466