1. Anionic additions to glycosyl iodides. 2. Neutral addition of alcohols to glycosyl iodides. 3. Glycosyl iodides in solid phase oligosaccharide synthesis

The usefulness of glycosyl iodides in carbohydrate chemistry has been demonstrated. Both anionic and neutral nucleophiles have been shown to react readily with glycosyl iodides as the glycosyl donor. High yields and stereoselectivity were obtained along with short reaction times. Anionic nucleophiles gave {dollar}beta{dollar} glycosides selectively, whereas neutral nucleophiles gave {dollar}alpha{dollar} glycosides in the presence of tetrabutylammonium iodide. Initial investigation of the applicability of these glycosidation conditions to solid phase oligosaccharide synthesis has been accomplished.