Desilylation under high pressure

Cleavage of tert-butyldiphenylsilyl (TBDPS) ether was examined under high pressure conditions (1.0 GPa) using HF/pyridine in DMF. This method proved to be exceptionally suitable for deprotecting the TBDPS group that resides at the sterically hindered position. Under these conditions, various types of other hydroxyl protecting groups (i.e. benzyl, p-methoxybenzyl, trityl, isopropylidene, cyclohexylidene, allyl, phthaloyl) as well as O- and S-glycosidic linkages were preserved.