This is the accepted manuscript. The final version is available at http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b01259. ; 2-Deoxy-2-fluoroglycosyl iodides are privileged glycosyl donors for the stereoselective preparation of 1-Nu-?-fluorosugars, which are useful reagents for chemical site-selective protein glycosylation. Ready access to such ?-fluorosugars enables the mild and efficient construction of well-defined fluoroglycoproteins. ; We thank the European Commission (Marie Curie CIG, O.B. and G.J.L.B.), MICINN, Spain (Juan de la Cierva Fellowship, O.B.), MINECO, Spain (CTQ2011-22872BQU) and Generalitat de Catalunya (M.S.) for generous financial support. We also thank Mr. Adri? Cardona-Benages (URV) for technical assis-tance. G.J.L.B. thanks the Royal Society (University Research Fellowship), Funda??o para a Ci?ncia a Tecnologia, Portugal (FCT Investigator), and the EPSRC for funding.