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Chemical name: (R)-Allylglycine (>98%, >99%ee) // Synonyms: (R)-2-Amino-pent-4-enoic acid, 4,5-Dehydro-D-norleucine (>98%, >99%ee)
|Molecular weight:||115,13 g/mol|
N-Allyloxycarbonyl (Alloc) are widely used protecting groups, i.e. for amines and amino acids, as they are quantitatively and very rapidly converted to free amino compounds by palladium. Deprotection of allyl (All) carboxylates and allyl aryl ethers can also be carried out accordingly.
All and Alloc are fully compatible with Fmoc/tBu and Boc/Bzl strategies, as well as with Z protecting groups.
Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to theselective 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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