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A novel strategy for the on-resin construction of disulfides via Allocam-protected cysteines. This palladium-mediated approach is mild and yields in pure disulfide bridged peptides with no observation of reduced peptide intermediates or S-allylated produc ts.
Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis; O. Dangles, F. Guibe, G. Balavoine, S. Lavielle and A. Marquet; The Journal of Organic Chemistry 1987; 52: 4984-4993. doi:10.1021/jo00231a027
Allylic protecting groups and their use in a complex environment part II: Allylic protecting groups and their removal through catalytic palladium π-allyl methodology; F. Guibé; Tetrahedron 1998; 54: 2967-3042. doi:http://dx.doi.org/10.1016/S0040-4020(97)10383-0
Mild non-transition metal catalyzed deprotection of N-allyloxycarbonyl amines; R. H. Szumigala Jr, E. Onofiok, S. Karady, J. D. Armstrong Iii and R. A. Miller; Tetrahedron letters 2005; 46: 4403-4405. doi:http://dx.doi.org/10.1016/j.tetlet.2005.04.064
Highly efficient removal of allyloxycarbonyl (Alloc) function provides a practical orthogonal protective strategy for carbohydrates; G. H. Zong, S. Q. Yan, X. M. Liang, J. J. Zhang, D. Q. Wang and F. Z. Kong; Chinese Chemical Letters 2009; 20: 127-130. doi:http://dx.doi.org/10.1016/j.cclet.2008.11.002
The Allyloxycarbonyl (Aloc) Moiety—Conversion of an Unsuitable into a Valuable Amino Protecting Group for Peptide Synthesis; H. Kunz and C. Unverzagt; Angewandte Chemie International Edition in English 1984; 23: 436-437. doi:10.1002/anie.198404361
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