I am currently designing a synthesis requiring the use of hydroxy protecting groups. The problem I am having is that the protecting group must be able to survive highly acidic conditions. I would have loved to use a TMBS protecting group since it can withstand LAH, lewis acids, and strong base; however, not acidic conditions. I really do not want to have to use a t-butyl ether protecting group, as its removal requires very harsh conditions. I will provide a scheme indicating all of the conditions I have proposed so far (this scheme is just a rough draft, so there are a few reagents that I have changed to be compatible with the reaction, but the general conditions should remain the same). Does anyone know any protecting groups that would match this criteria? I am only referring to replacing the TMBS protecting group on the second intermediate.