Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry VIII. A simple, practical method for the preparation of glycosyl iodides from per-O-acetyl or other derivatives of carbohydrates

Treatment of per-O-acetylated mono-, and di-saccharides with hexamethyldisilane (HMDS) and iodine at ambient temperature results in the formation of the respective glycosyl iodides in near quantitative yield. This reagent system also enables direct conversion of O-glycosides, such as 2-(trimethylsilyl)ethyl and benzyl glycosides of mono-, di- and tri-saccharides, to the respective glycosyl iodides in a simple and efficient manner. The reaction is homogeneous, relatively fast and yields product that is pure enough for most subsequent applications.