Skip to main content
SpringerLink
Log in

1-(t-Butyldimethylsilyloxy) benzotriazole (TBDMS-OBt): A new and novel reagent for the synthesis of peptides

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Lott, R. S., Chauhan, V. S. and Stammer, C. H., J. Chem. Soc. Chem. Commun., (1979) 495.

  2. Kaiser Sr., E., Kubaik, T. M., Tam, J. P. and Merrifield, R. B., Tetrahedron Lett., 29 (1998) 303.

    Google Scholar 

  3. Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Pept. Prot. Res., 45 (1995) 377.

    Google Scholar 

  4. Mattern, R. H., Gunasekara, S. P. and Mcconnel, O. J., Tetrahedron Lett., 38 (1997) 2197.

    Google Scholar 

  5. Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1972) 69.

    Google Scholar 

  6. Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1992) 6190.

    Google Scholar 

  7. 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.

    Google Scholar 

  8. Carpino, L. A., Beyermann, M., Wensehuh, H. and Bienert, M., Acc. Chem. Res., 29 (1996) 268.

    Google Scholar 

  9. Albercio, F., Chinchilla, R., Dodsworth, D. J. and Najera, C., Org. Prep. Proc. Int., 33 (2001) 203.

    Google Scholar 

  10. Carpino, L. A., Chao, H.-G., Beyermann, M. and Bienert, M., J. Org. Chem., 56 (1991) 2635.

    Google Scholar 

  11. Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Peptide Protein Res., 44 (1994) 24.

    Google Scholar 

  12. Suresh Babu, V. V. and Gopi, H. N., Tetrahedron Lett., 39 (1998) 1049.

    Google Scholar 

  13. Gopi, H. N.and Suresh Babu, V. V., Ind. J. Chem., 37B (1998) 394.

    Google Scholar 

  14. Gopi, H. N. and Suresh Babu, V. V., Tetrahedron Lett., 39 (1998) 9769.

    Google Scholar 

  15. Suresh Babu, V. V. and Ananda, K., Lett. Pept. Sci., 7 (2000) 41.

    Google Scholar 

  16. Carpino, L. A., Ionescu, D., El-Faham, A., Wenschuh, H., Bienert, M. and Beyermann, M., Tetrahedron Lett., 39 (1998) 241.

    Google Scholar 

  17. Brunissen, A., Ayoub, M. and Laviella, S., Tettrahedron Lett., 37 (1996) 6713.

    Google Scholar 

  18. Leggio,ed A., Liguori, A., Procopio, A. and Sindona, G., J. Chem. Soc. Perkin Trans., 1 (1997) 1969

    Google Scholar 

  19. Suresh Babu, V. V., Ananda, K. and Vasanthakumar, G.-R., J. Chem. Soc. Perkin Trans., 1 (2000) 4328.

    Google Scholar 

  20. Carpino, L. A., J. Org. Chem., 53 (1988) 875.

    Google Scholar 

  21. Ananda, K. and Suresh Babu, V. V., J. Pept. Res., 57 (2001) 223.

    Google Scholar 

  22. Albericio, F., Bofill, J. M., El-Faham, A. and Kates, S. A., J. Org. Chem., 63 (1998) 9678

    Google Scholar 

  23. 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.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India

    Subramanyam J. Tantry & Vommina V. Suresh Babu

Authors
  1. Subramanyam J. Tantry
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vommina V. Suresh Babu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vommina V. Suresh Babu.

Rights and permissions

Reprints 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

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1021307501833

Search

Navigation