Preparation of Anhydroalditols from Commodity Carbohydrates

A practical process for the preparation of anhydroalditols from commodity carbohydrates has been described. Reductive cleavage of the glycosidic linkage in perallylated carbohydrates with triethylsilane gave the protected anhydroalditols, which were then deallylated using a PdCl2-CuCl2-Activated Charcoal system. Valuable anhydroalditols, such as 1,5-anhydro-D-glucitol, 1,5-anhydro-D-mannitol, 2,5-anhydro-D-glucitol, 2,5-anhydro-D-mannitol and 1,4-anhydro-Dribitol, were prepared in high yields and purity from carbohydrates, such as glucose, mannose, ribose, sucrose, cellulose, starch and levan.