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Tert-Butyldiphenylsilyl
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Tert-Butyldiphenylsilyl : ウィキペディア英語版
Tert-Butyldiphenylsilyl

''tert''-Butyldiphenylsilyl, also known as TBDPS or TPS, is a protecting group for alcohols. Its formula is C16H19Si-.〔http://www.organic-chemistry.org/protectivegroups/hydroxyl/tbdps-ethers.htm〕
==Development==
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:



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.〔Hanessian, S; Lavelle, P; Can. J. Chem., 53, 19, 2975-2977〕

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