Reaction with acids or fluorides such as tetra-n-butylammonium fluoride removes the silyl group when protection is no longer needed. Larger substituents increase resistance to hydrolysis, but also make introduction of the silyl group more difficult.
In acidic media, the relative resistance is:
:TMS (1) < TES (64) < TBS (20 000) < TIPS (700,000) < TBDPS (5,000,000)
In basic media, the relative resistance is:
:TMS (1) < TES (10-100) < TBS~TBDPS (20 000) < TIPS (100,000)