dc.creator | Suppo J.-S. | |
dc.creator | De Sant'Ana D.P. | |
dc.creator | Dias L.C. | |
dc.creator | De Figueiredo R.M. | |
dc.creator | Campagne J.-M. | |
dc.date | 2014 | |
dc.date | 2015-06-25T18:01:03Z | |
dc.date | 2015-11-26T15:02:49Z | |
dc.date | 2015-06-25T18:01:03Z | |
dc.date | 2015-11-26T15:02:49Z | |
dc.date.accessioned | 2018-03-28T22:13:41Z | |
dc.date.available | 2018-03-28T22:13:41Z | |
dc.identifier | | |
dc.identifier | Synthesis (germany). Georg Thieme Verlag, v. 46, n. 22, p. 3075 - 3084, 2014. | |
dc.identifier | 397881 | |
dc.identifier | 10.1055/s-0034-1379004 | |
dc.identifier | http://www.scopus.com/inward/record.url?eid=2-s2.0-84911899566&partnerID=40&md5=05b9f185e7170dfec29d511aa6697047 | |
dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/87484 | |
dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/87484 | |
dc.identifier | 2-s2.0-84911899566 | |
dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1256462 | |
dc.description | 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. | |
dc.description | 46 | |
dc.description | 22 | |
dc.description | 3075 | |
dc.description | 3084 | |
dc.description | Barany, G., Merrifield, R.B., (1977) J. Am. Chem. Soc., 99, p. 7363 | |
dc.description | Barany, G., Albericio, F., (1985) J. Am. Chem. Soc., 107, p. 4936 | |
dc.description | Isidro-Llobet, A., Álvarez, M., Albericio, F., (2009) Chem. Rev., 109, p. 2455. , references cited therein | |
dc.description | Arrieta, A., Garcia, T., Palomo, C., (1982) Synth. Commun., 12, p. 1139 | |
dc.description | Balasubramaniyan, V., Bhatia, V.G., Wagh, S.B., (1983) Tetrahedron, 39, p. 1475 | |
dc.description | Widmer, U., (1983) Synthesis, p. 135 | |
dc.description | Brook, M.A., Chan, T.H., (1996) Synthesis, p. 201 | |
dc.description | Arai, I., Muramatsu, I., (1983) J. Org. Chem., 48, p. 121 | |
dc.description | Koåodziejczyk, A.M., Slebjoda, M., (1984) Synthesis, p. 866 | |
dc.description | Lalezari, I., Lalezari, P., (2014), U.S. Pat. Appl. PublSieber, P., (1977) Helv. Chim. Acta, 60, p. 2711 | |
dc.description | 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 | |
dc.description | Schmidt, U., Zäh, M., Lieberknecht, A., (1991) J. Chem. Soc., Chem. Commun., p. 1002. , With DCC | |
dc.description | Fécourt, F., Sapi, J., Bourguet, E., (2010) Synlett, p. 399. , With DIC | |
dc.description | Boger, D.L., Yohannes, D., (1990) J. Org. Chem., 55, p. 6000 | |
dc.description | Wang, T., Danishefsky, S.J., (2012) J. Am. Chem. Soc., 134, p. 13244 | |
dc.description | Banala, S., Ensle, P., Süssmuth, R.D., (2013) Angew. Chem. Int. Ed., 52, p. 9518 | |
dc.description | Schnabel, E., Klostermeyer, H., Berndt, H., (1971) Justus Liebigs Ann. Chem., 749, p. 90 | |
dc.description | Akaji, K., Fujii, N., Yajima, H., (1985) Chem. Pharm. Bull., 33, p. 173 | |
dc.description | 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 | |
dc.description | Bachi, M.D., Breiman, R., (1980) J. Chem. Soc., Perkin Trans. 1, p. 11 | |
dc.description | Pfizenmayer, A.J., Ramanjulu, J.M., Vera, M.D., Ding, X., Xiao, D., Chen, W.-C., Joullié, M.M., (1999) Tetrahedron, 55, p. 313 | |
dc.description | 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 | |
dc.description | Frérot, E., Coste, J., Pantaloni, A., Dufour, M.-N., Jouin, P., (1991) Tetrahedron, 47, p. 259 | |
dc.description | Campagne, J.-M., Coste, J., Jouin, P., (1993) Tetrahedron Lett., 34, p. 6743 | |
dc.language | en | |
dc.publisher | Georg Thieme Verlag | |
dc.relation | Synthesis (Germany) | |
dc.rights | aberto | |
dc.source | Scopus | |
dc.title | 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 | |
dc.type | Artículos de revistas | |