Protecting groups constitute one of the most powerful tools in the synthesis of multifunctional compounds such as oligosaccharides and peptides to temporarily mask sites of similar reactivity. Due to the inherent low atom economy it is desirable to minimize the use of protecting groups although the efficiency of proper protecting group strategy is still unprecedented. Protecting groups should ideally meet several criteria; (i) easy and high yielding to introduce, (ii) be stable under a wide range of reaction conditions and (iii) to be removed under mild conditions. We have previously developed highly efficient protocols for removing both allylethers and tosylamides using SmI2/Et3N/H2O [1].We have now developed 3,5-bis-(trifluoromethyl) benzylcarbamate as a protecting group that can be selectively cleaved under mild SET conditions while it is unusually stable under hydrogenation conditions. (Figure 1) In this respect, this group has a unique property that is not shared with any of the existing carbamate protecting groups (cbz, Troc, Aloc, Boc etc).Figure 1  . Orthogonal deprotection of the cbz-group using Pd/C or the 3,5-bis-(trifluoromethyl) benzylcarbamate using SmI2/Et3N/H2O.1(a) Dahl�n, A.; Sundgren, A.; Lahmann, M.; Oscarson, S. and Hilmersson, G., Org. Lett. 2003  , 4085. (b) Ankner, T; Hilmersson, G., Org. Lett., 2009  , 11, 503.

Introduction of a new single electron transfer sensitive protecting group

243rd National Meeting (2012)

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