tert-Butyldiphenylsilyl

It was designed to supersede the use of Corey's tert-butyldimethylsilyl as a protecting group for alcohols: In addition to retaining all the known features that are associated with silyl ethers, such as their ease and selectivity of formation, their adaptability to various analytical techniques, and their compatibility with a variety of conditions or synthetic transformations in organic chemistry, the [TBDPS] group offers some unique and novel features that constitute a significant improvement over the existing related groups, and warrants their communication at this time.

The group is unaffected by treatment with 80% acetic acid, which catalyses the deprotection of O-tetrapyranyl, O-trityl and O-tert-butyldimethylsilyl ethers.

This can be thought of as arising from the extra steric bulk of the groups surrounding the silicon atom.

This might involve using the triflate or the less reactive chloride of TBDPS along with a mild base such as 2,6-lutidine or pyridine and potentially a catalyst such as DMAP or imidazole.

The increased stability towards acidic hydrolysis and nucleophilic species allows for the TBDPS groups in a substrate to be retained while other silyl ethers are removed.