Sodium Hydride/Hexamethylphosphoric Triamide: A New and Efficient Reagent Towards the Synthesis of Protected 1,2- and 5,6-Enopyranosides.

A new method for the elimination of hydrogen halides and p-toluenesulfonic acid from sugar moieties using sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) at room temperature is reported. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically hindered starting materials, and not only from halides, but also tosylates.