10.1248/cpb.55.861
The study focuses on the use of mesoporous silicas, specifically MCM-41, for the selective deprotection of silyl groups in organic synthesis. The researchers aimed to achieve an environmentally benign process by using a heterogeneous catalyst that simplifies the work-up process and can be recycled. The chemicals used in the study include various silyl ethers of dodecanol and 1,4-butanediol, as well as different mesoporous silicas such as MCM-41, FSM-16, and HMS. These silyl ethers serve as substrates for the deprotection process, while the mesoporous silicas act as solid acid catalysts to selectively remove the triethylsilyl (TES) group in the presence of a t-butyldimethylsilyl (TBDMS) group. The study also explored the recyclability of FSM-16 by re-calcination after each reaction cycle, demonstrating its potential for sustainable use in organic synthesis.
10.1021/jo00246a038
The research explores the development and evaluation of a new class of alcohol-protecting groups, specifically the alkoxydiphenylsilyl ethers, with a focus on tert-butoxydiphenylsilyl ethers. The purpose of this study was to identify a protecting group that offers both acid stability and high fluoride reactivity, which can be selectively cleaved or retained in the presence of other silyl ethers. The key chemicals used in the research include tert-butoxydiphenylsilyl chloride, various alcohols (such as n-dodecanol, 2-octanol, and 1-methylcyclohexanol), triethylamine, and tetra-n-butylammonium fluoride. The study found that tert-butoxydiphenylsilyl ethers exhibit excellent hydrolytic stability and enhanced fluoride reactivity, making them useful for protecting primary alcohols and for selective deprotection in the presence of other silyl ethers. The research concludes that these ethers are a valuable addition to the existing repertoire of silyl protecting groups, particularly when fluoride sensitivity is desired, and they offer advantages such as selective protection of primary alcohols and compatibility with a wide range of synthetic transformations.
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