Tert-Butyldiphenylsilyl
tert-Butyldiphenylsilyl, also known as TBDPS, is a protecting group for alcohols. Its formula is C16H19Si-.
The tert-butyldiphenylsilyl group was first suggested as a protecting group by Hanessian and Lavalle in 1975. 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 novel features that they highlight are the increased resistance to acidic hydrolysis and increased selectivity towards protection of primary hydroxyl groups. The group is unaffected by treatment with 80% acetic acid, which catalyses the deprotection of O-tetrapyranyl, O-trityl and O-tert-butyldimethylsilyl ethers. It is also unaffected by 50% trifluoroacetic acid (TFA), and survives the harsh acidic conditions used to install and remove isopropylidene or benzylidene acetals.
The TBDPS group is prized for its increased stability towards acidic conditions and nucleophilic species over the other silyl ether protecting groups. This can be thought of as arising from the extra steric bulk of the groups surrounding the silicon atom. The protecting group is easily introduced by using the latent nucleophilicity of the hydroxyl group and an electrophilic source of TBDPS. 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.
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