Abstract
Synthesis and use of 1-(t-butyldimethylsilyloxy)benzotriazole (TBDMS-OBt) in the coupling of Fmoc-amino acid chlorides to amino free amino acid esters in homogeneous solution phase is described. The coupling required no addition of base and was fast and racemization free. Work up and isolation of products were easy. Yield, purity and 1H NMR analysis of peptides, synthesised by this method, were satisfactory.
Similar content being viewed by others
References
Lott, R. S., Chauhan, V. S. and Stammer, C. H., J. Chem. Soc. Chem. Commun., (1979) 495.
Kaiser Sr., E., Kubaik, T. M., Tam, J. P. and Merrifield, R. B., Tetrahedron Lett., 29 (1998) 303.
Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Pept. Prot. Res., 45 (1995) 377.
Mattern, R. H., Gunasekara, S. P. and Mcconnel, O. J., Tetrahedron Lett., 38 (1997) 2197.
Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1972) 69.
Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1992) 6190.
Carpino, L. A., Cohen, B. J., Kenton, E., Stephen Jr., S., Sadat-Aalee, S. Y. Tien, J.-H. and Lengridge, D. C., J. Org. Chem., 51 (1986) 3732.
Carpino, L. A., Beyermann, M., Wensehuh, H. and Bienert, M., Acc. Chem. Res., 29 (1996) 268.
Albercio, F., Chinchilla, R., Dodsworth, D. J. and Najera, C., Org. Prep. Proc. Int., 33 (2001) 203.
Carpino, L. A., Chao, H.-G., Beyermann, M. and Bienert, M., J. Org. Chem., 56 (1991) 2635.
Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Peptide Protein Res., 44 (1994) 24.
Suresh Babu, V. V. and Gopi, H. N., Tetrahedron Lett., 39 (1998) 1049.
Gopi, H. N.and Suresh Babu, V. V., Ind. J. Chem., 37B (1998) 394.
Gopi, H. N. and Suresh Babu, V. V., Tetrahedron Lett., 39 (1998) 9769.
Suresh Babu, V. V. and Ananda, K., Lett. Pept. Sci., 7 (2000) 41.
Carpino, L. A., Ionescu, D., El-Faham, A., Wenschuh, H., Bienert, M. and Beyermann, M., Tetrahedron Lett., 39 (1998) 241.
Brunissen, A., Ayoub, M. and Laviella, S., Tettrahedron Lett., 37 (1996) 6713.
Leggio,ed A., Liguori, A., Procopio, A. and Sindona, G., J. Chem. Soc. Perkin Trans., 1 (1997) 1969
Suresh Babu, V. V., Ananda, K. and Vasanthakumar, G.-R., J. Chem. Soc. Perkin Trans., 1 (2000) 4328.
Carpino, L. A., J. Org. Chem., 53 (1988) 875.
Ananda, K. and Suresh Babu, V. V., J. Pept. Res., 57 (2001) 223.
Albericio, F., Bofill, J. M., El-Faham, A. and Kates, S. A., J. Org. Chem., 63 (1998) 9678
Recently 1-(trimethylsilylmethyl) benzotriazole was used in homologation of carboxylic acids as a safe alternative to the Arndt-Eistert reaction by Katritzky, R., Zhang, S., Hussein, A. H. M. and Fang, Y., J. Org. Chem., 66 (2001) 5606.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tantry, S.J., Babu, V.V.S. 1-(t-Butyldimethylsilyloxy) benzotriazole (TBDMS-OBt): A new and novel reagent for the synthesis of peptides. Letters in Peptide Science 9, 35–41 (2002). https://doi.org/10.1023/A:1021307501833
Issue Date:
DOI: https://doi.org/10.1023/A:1021307501833