853654-22-5Relevant academic research and scientific papers
New strategies for protecting group chemistry: Synthesis, reactivity, and indirect oxidative cleavage of para-siletanylbenzyl ethers
Tlais, Sami F.,Lain, Hubert,House, Sarah E.,Dudley, Gregory B.
supporting information; experimental part, p. 1876 - 1885 (2009/07/01)
Reported herein is a new entry in the growing arsenal of arylmethyl ether protecting groups. The parasiletanylbenzyl (PSB) ether is electronically similar to the benzyl ether. Cleavage of the PSB ether is accomplished under mild conditions-involving alkaline hydrogen peroxide - that are unique among cleavage protocols for arylmethyl ethers. Furthermore, the PSB group affords the user new flexibility in the implementation of protecting group strategies that revolve around multiple arylmethyl ether protecting groups. In addition to hydrogen peroxide-based cleavage protocols, conversion of a PSB ether into a para-methoxybenzyl (PMB) ether and assembly of a PSB ether from a pre-existing para-bromobenzyl (PBB) ether are described. Finally, a new reagent for installing PSB ethers under neutral "mix and heat" conditions is reported.
The para-siletanylbenzyl (PSB) ether: A peroxide-cleavable protecting group for alcohols and phenols
Lam, Hubert,House, Sarah E.,Dudley, Gregory B.
, p. 3283 - 3285 (2007/10/03)
A novel arylmethyl protecting group that is electronically similar to benzyl (Bn) but that can be cleaved under mild oxidizing conditions in the presence of para-methoxybenzyl (PMB) is described herein. para-Siletanylbenzyl (PSB) ethers are formed in one or two steps from the corresponding alcohols and cleaved in one or two steps with basic peroxide. Alcohols and phenols have been protected in good yields and deprotected cleanly under mild oxidative conditions.
