tert-Butyldiphenylsilyl, also known as TBDPS, is a protecting group for alcohols. Its formula is C 16 H 19 Si-. [1] The tert -butyldiphenylsilyl group was first suggested as a protecting group by Hanessian and Lavallée in 1975. It was designed to supersede the use of Corey's tert -butyldimethylsilyl as a protecting group for alcohols:

Oct 6, 2021 · The tert -butyldiphenylsilyl (TBDPS) protection has been commonly used for primary hydroxyl groups in carbohydrate chemistry (1). A primary hydroxyl group can be preferentially silylated using TBDPSCl and imidazole in the presence of other secondary hydroxyl groups (2).

Various tert -butyldimethylsilyl (TBDMS) ethers as well as tert -butyldiphenylsilyl (TBDPS) ethers can be easily deprotected by employing a catalytic amount of acetyl chloride in dry MeOH in good yields. This mild and convenient method tolerates various other protecting groups and does not lead to acylated or chlorinated byproducts.

Jun 17, 2015 · Tetrahydropyranyl (THP) ethers are also useful protecting groups for alcohols. What Would Be A Chemical Equivalent of “Painter’s Tape”? 1. When Alcohols Get In the Way. As we’ve seen in previous posts in this series, alcohols are very versatile functional groups that participate in a variety of reactions.

Silyl groups are typically deprotected with a source of fluoride ion. The Si–F bond stength is about 30 kcal/mol stronger than the Si–O bond. Monosilylation of symmetrical diols is possible, and useful. = 2-6,10 McDougal, P.G.; Rico, J.G.; Oh, Y.; Condon, B. D. J. Org. Chem. 1986, 51, 3388.

TBDMS ethers can be cleaved selectively in the presence of isopropylidine, Bn, Ac, Bz, THP, and TBDPS groups using tetrabutylammonium tribromide in methanol. This method is high yielding, fast, clean, safe, and cost-effective.

Jun 11, 1993 · Reaction of the alcohol and tBDPSCl in DMF with AgN03, NH4NO3, or NH4C104 provides good yields of the corresponding silyl ethers.

Feb 26, 2021 · TBDPS保护基对许多与TBDMS保护基不相容的试剂显出比TBDMS基团更好的稳定性。 TBDMS基团在酸性条件下不易迁移。 碱性稳定条件：1、K2CO3 /CH3OH；2、9M氨水、60℃、2h；3、MeONa（cat.）/CH3OH、25℃、24h稳定。 酸性稳定条件：1、80%乙酸稳定（可用于脱除醚中TBDMS，三苯甲基，四氢吡喃保护基）；2、HBr/AcOH，12℃，2min；3 …

The clean deprotection or desilylation of a silyl-protected functional group is essential to its utility.

叔丁基二苯基氯硅烷又称硅烷保护剂，其作用是硅烷基取代化合物中的活泼氢 (如羟基、羧基和氨基中的氢)，生成稳定的中间体；然后，该中间体的其他基团在进行某些反应；反应结束后，通过水解反应，脱除硅烷基，使原被硅烷基保护的基团再生，合成出某些特定化合物。 由于硅烷的保护和去保护反应的转化率高，甚至是定量反应，使其广泛应用于有机合成中，特别是药物合成中。