Artículos de revistas
Efficient And Practical Procedure For The Esterification Of The Free α-carboxylic Acid Of Amino Acid Residues With β-(trimethylsilyl)ethoxymethyl Chloride And Triisopropylsilyl Chloride
Registro en:
Synthesis (germany). Georg Thieme Verlag, v. 46, n. 22, p. 3075 - 3084, 2014.
397881
10.1055/s-0034-1379004
2-s2.0-84911899566
Autor
Suppo J.-S.
De Sant'Ana D.P.
Dias L.C.
De Figueiredo R.M.
Campagne J.-M.
Institución
Resumen
An efficient and practical procedure for the free α-carboxylic acid esterification of amino acid residues with β-(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride is described. The reaction takes place under mild conditions and the expected protected amino acids are obtained in good to excellent yields. Our method provides a useful alternative for the C-terminal carboxylic acid protection of amino acids and peptides. Moreover, the removal of such protection was also achieved under mild conditions, without affecting either the other protecting groups at the α-amino moiety and side chains or the optical integrity at the α-position of the amino acid residues. Examples of their use in peptide synthesis are also illustrated. 46 22 3075 3084 Barany, G., Merrifield, R.B., (1977) J. Am. Chem. Soc., 99, p. 7363 Barany, G., Albericio, F., (1985) J. Am. Chem. Soc., 107, p. 4936 Isidro-Llobet, A., Álvarez, M., Albericio, F., (2009) Chem. Rev., 109, p. 2455. , references cited therein Arrieta, A., Garcia, T., Palomo, C., (1982) Synth. Commun., 12, p. 1139 Balasubramaniyan, V., Bhatia, V.G., Wagh, S.B., (1983) Tetrahedron, 39, p. 1475 Widmer, U., (1983) Synthesis, p. 135 Brook, M.A., Chan, T.H., (1996) Synthesis, p. 201 Arai, I., Muramatsu, I., (1983) J. Org. Chem., 48, p. 121 Koåodziejczyk, A.M., Slebjoda, M., (1984) Synthesis, p. 866 Lalezari, I., Lalezari, P., (2014), U.S. Pat. Appl. PublSieber, P., (1977) Helv. Chim. Acta, 60, p. 2711 Sieber, P., Andreatta, R.H., Eisler, K., Kamber, B., Riniker, B., Rink, H., (1977) Peptides, Proceedings of the 5th American Peptide Symposium, p. 543. , Goodman M. Meienhofer J. Wiley New York Schmidt, U., Zäh, M., Lieberknecht, A., (1991) J. Chem. Soc., Chem. Commun., p. 1002. , With DCC Fécourt, F., Sapi, J., Bourguet, E., (2010) Synlett, p. 399. , With DIC Boger, D.L., Yohannes, D., (1990) J. Org. Chem., 55, p. 6000 Wang, T., Danishefsky, S.J., (2012) J. Am. Chem. Soc., 134, p. 13244 Banala, S., Ensle, P., Süssmuth, R.D., (2013) Angew. Chem. Int. Ed., 52, p. 9518 Schnabel, E., Klostermeyer, H., Berndt, H., (1971) Justus Liebigs Ann. Chem., 749, p. 90 Akaji, K., Fujii, N., Yajima, H., (1985) Chem. Pharm. Bull., 33, p. 173 Huffman, G.W., Gesellchen, P.D., Turner, J.R., Rothenberger, R.B., Osborne, H.E., Miller, F.D., Chapman, J.L., Queener, S.W., (1992) J. Med. Chem., 35, p. 1897 Bachi, M.D., Breiman, R., (1980) J. Chem. Soc., Perkin Trans. 1, p. 11 Pfizenmayer, A.J., Ramanjulu, J.M., Vera, M.D., Ding, X., Xiao, D., Chen, W.-C., Joullié, M.M., (1999) Tetrahedron, 55, p. 313 See also ref. 12For one example of chemoselective OBn ether deprotection, see ref. 13Coste, J., Le-Nguyen, D., Castro, B., (1990) Tetrahedron Lett., 31, p. 205 Frérot, E., Coste, J., Pantaloni, A., Dufour, M.-N., Jouin, P., (1991) Tetrahedron, 47, p. 259 Campagne, J.-M., Coste, J., Jouin, P., (1993) Tetrahedron Lett., 34, p. 6743