text: Glycosyl iodides were first introduced for use in glycosylation reactions in 1901 by Koenigs and Knorr although were often considered too reactive for synthetic use.  Recently several research groups have shown these donors to have unique reactive properties and can differ from other glycosyl chlorides or bromides with respect to reaction time, efficiency, and stereochemistry. Glycosyl iodides may be made under a variety of conditions, one method of note is the reaction of a 1-O-acetylpyranoside with TMSI.
  Iodide donors may typically be activated under basic conditions to give β-glycosides with good selectivity.  The use of tetraalkylammonium iodide salts such as tetrabutylammonium iodide (TBAI) allows for in-situ anomerization of the α-glycosyl halide to the β-glycosyl halide and provides the α-glycoside in good selectivity.