96013-69-3Relevant articles and documents
Synthetic Versatility of Lipases: Application for Si-O Bond Formation and Cleavage
Brondani, Patrícia Bulegon,Mittersteiner, Mateus,Voigt, Morgana Aline,Klinkowski, Bruna Heloisa,Riva Scharf, Dilamara,De Jesus, Paulo Cesar
, p. 477 - 485 (2019/01/10)
Several commercially available lipases were examined in a study on O-Si bond formation and cleavage applying silicon-based protecting groups and alcohols or the corresponding silyl ethers. With regard to deprotection, from silyl ether to the corresponding alcohol, only the solvent and the lipase were necessary. The influence of the protecting group, the lipase source, and the substituent was investigated to optimize the results. The TMS moiety could be removed in 24 hours of reaction at room temperature in aqueous systems (conv. up to 99%, depending on the substrate and lipase). The reverse reactions, that is, with the protection of the alcohols, were carried out in hexane using different silyl chlorides. The TMS, TES, and TBS moieties were successfully inserted in the primary and secondary alcohols without the need for dry conditions or an inert atmosphere, presenting conversions of up to 99%, depending on the substrate.
Tert-Butyldimethylsilyl Amine (TBDMS-NH2): A Mild and Green Reagent for the Protection of Benzyl Alcohols, Phenols, and Carboxylic Acids under Solvent-Free Conditions
Duczynski, Jeremy A.,Fuller, Rebecca,Stewart, Scott G.
, p. 1172 - 1179 (2016/10/13)
Herein, we present the use of the tert-butyldimethylsilyl amine (TBDMS-NH2) as a silylating reagent for phenols, benzyl alcohols, and carboxylic acids. Unlike other silyl protection reactions, this reported process with TBDMS-NH2 does not involve the form
An Efficient and Highly Chemoselective Method to Desilylate Silyl Ethers
Lee, Adam Shih-Yuan,Yeh, Hsiu-Chih,Yeh, Ming-Kuo,Tsai, Ming-Hung
, p. 919 - 922 (2007/10/03)
An efficient and highly chemoselective desilylating method is described.Trimethylsilyl ethers (0.25 M) in a CH3OH/CCl4 (1:1) solvent mixture are deprotected to their corresponding alcohols with ultrasound in a commercial ultrasonic cleaning bath.Selective deprotection of tert-butyldimethylsilyl ethers of benzyl alcohols and phenols is achieved under ultrasonic conditions.We deprotected also tert-butyldimethylsilyl ethers of primary alcohols, whereas tert-butyldimethylsilyl ethers of secondary and tertiary alcohols are stable under these conditions. - Key words: Sonochemistry; Ultrasound; Cavitation; Desilylation; Chemoselection; Deprotection.
Selective removal of phenolic and alcoholic silyl ethers
Prakash, Chandra,Saleh, Samir,Blair, Lan A.
, p. 7565 - 7568 (2007/10/02)
Potassium carbonate/Kriptofix 222 and pyridinium p-toluenesulfonate or BF3-etherate have been found to remove the tert-butyldimethylsilyl group from phenolic and alcoholic silyl ethers, respectively. This methodology should find wide applicability in complex organic synthesis.
