Propanephosphonic acid anhydride (T3P®) - A benign reagent for diverse applications inclusive of large-scale synthesis

Synthesis (Germany)

Volumn 45, Issue 12, 2013, Pages 1569-1601

  Vishwanatha, T M ^a   Panguluri, Nageswara Rao ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

coupling; large scale synthesis; racemization; rearrangement

Indexed keywords

AMINO ACID DERIVATIVES; CARBON-CARBON BOND FORMATION; FUNCTIONAL GROUP TRANSFORMATIONS; GENERAL APPLICATIONS; LARGE SCALE SYNTHESIS; RACEMIZATION; REARRANGEMENT; REARRANGEMENT REACTIONS;

AMINO ACIDS; CHEMICAL BONDS; CONDENSATION REACTIONS; COUPLING AGENTS; COUPLINGS; DEHYDRATION; FUNCTIONAL GROUPS; PEPTIDES;

SYNTHESIS (CHEMICAL);

AMINO ACID DERIVATIVE; CARBON; CARBOXYLIC ACID ACTIVATOR; DEHYDRATING AGENT; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; PEPTIDE; PEPTIDOMIMETIC AGENT; PEVRIEOWPANEPHOSPHONIC ACID ANHYDRIDE; REAGENT; UNCLASSIFIED DRUG;

BIOCHEMISTRY; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ORGANIC CHEMISTRY; OXIDATION; REVIEW; SYNTHESIS;

EID: 84878778171     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0033-1338989     Document Type: Review

References (47)

1. Wissmann H., Kleiner H.-J. Angew. Chem.: 1980; 92 133
2. Wissmann H. Phosphorus Sulfur Relat. Elem.: 1987; 30 645
3. Escher R., Buning P. Angew. Chem. Int. Ed.: 1986; 25 277
4. Wissmann H., König W., Geiger R. In Peptides: Structure and Funciton. Proceedings of the 8th American Peptide Symposium. Hruby V. J., Rich D. H. Pierce Chem. Co Rockford (IL, USA): 1983; 111
5. Wehner M., Kirschbaum B., Deutscher L., Wagner H. J., Hoessl H. PCT Int. Appl. WO 2005014604: 2005;; Chem. Abstr. 2005, 142, 198208.
6. Schwarz M. Synlett: 2000; 1369
7. Llanes García A. L. Synlett: 2007; 1328
8. Coupling Agent T3P-The Water Scavenger http://www.euticals.com./ attachments/082-EUTICALS-T3P-Coupling-Agents-2012-final-web.pdf
9. Koch P., Vedder C., Schaffer T. Chim. Oggi/Chem. Today: 2008; 26 (Suppl. 4) 6
10. Lutz J., Musiol H.-J, Moroder L. In Houben-Weyl: Synthesis of Peptides and Peptidomimetics. Vol. E22a Goodman M., Felix A., Moroder L., Toniolo C. Georg Thieme Stuttgart: 2004; 427
11. Sewald N., Jakubke H. D. In Peptides: Chemistry and Biology. Wiley-VCH Weinheim: 2002
12. El-Faham A., Albericio F. Chem. Rev.: 2011; 111 6557
13. Wenger R. M. Helv. Chim. Acta: 1984; 67 502
14. Klose J., Bienert M., Mollenkopf C., Wehle D., Zhang C.-W, Carpino L. A., Henklein P. Chem. Commun.: 1999; 1847
15. Basavaprabhu Narendra N., Lamani R. S., Sureshbabu V. V. Tetrahedron Lett.: 2010; 51 3002
16. Sureshbabu V. V., Ananda K., Vasanthakumar G. R. J. Chem. Soc., Perkin Trans. 1: 2000; 4328
17. Katritzky A. R., Widyan K., Kirichnko K. J. Org. Chem.: 2007; 72 5802
18. Patil B. S., Vasanthakumar G. R., Sureshbabu V. V. J. Org. Chem.: 2003; 68 7274
19. Hemantha H. P., Narendra N., Sureshbabu V. V. Tetrahedron: 2012; 68 9491
20. Rao Y., Nagorny P., Hayashida J., Danishefsky S. J. Tetrahedron Lett.: 2009; 50 6684
21. Wu X., Stockdill J. L., Wang P., Danishefsky S. J. J. Am. Chem. Soc.: 2010; 132 4098
22. Raibaut L., Ollivier N., Melnyk O. Chem. Soc. Rev.: 2012; 41 7001
23. Kent S. B. H. Chem. Soc. Rev.: 2009; 38 338
24. Madhu C. Basavaprabhu Vishwanatha T. M., Sureshbabu V. V. Tetrahedron Lett.: 2012; 53 1405
25. Crich D., Sasaki K., Rahaman Md Y., Bowers A. A. J. Org. Chem.: 2009; 74 3886
26. Benotoin N. L. Chemistry of peptide synthesis. Taylor and Francis New York: 2006; 197 242
27. th European Peptide Symposium. Brunfeldt K. Scriptor Copenhagen: 1980; 174
28. Constable D. J. C, Dunn P. J., Hayler J. D., Humphrey G. R., Leazer J. L., Linderman R. J. Jr, Lorenz K., Manley J., Pearlman B. A., Wells A., Zaks A., Zhang T. Y. Green Chem.: 2007; 9 411
29. Allen C. L., Williams J. M. J. Chem. Soc. Rev.: 2011; 3405
30. Han S.-Y, Kim Y.-A. Tetrahedron: 2004; 60 2447
31. Montalbetti C. A. G. N, Falque V. Tetrahedron: 2005; 61 10827
32. Newcomb M. Tetrahedron: 1993; 49 1151
33. Hartung J., Hiller M., Schwarz M., Svobola I., Fuess H. Liebigs Ann.: 1996; 157
34. Barton D. H. R, Blundell P., Jaszberenyi J. C. J. Am. Chem. Soc.: 1991; 113 6933
35. Hartung J., Schwarz M. Synlett: 2000; 371
36. Patterson J. E., Ollman I. R., Cravatt B. F., Boger D. L., Wong C.-H, Lerner R. A. J. Am. Chem. Soc.: 1996; 118 5938
37. Vasanthakumar G. R., Sureshbabu V. V. Tetrahedron Lett.: 2003; 44 4099
38. Ech-Chahad A., Minassi A., Berton L., Appendino G. Tetrahedron Lett.: 2005; 46 5113
39. Nahm S., Weinreb S. M. Tetrahedron Lett.: 1981; 22 3815
40. Balasubhramanium S., Aidhen I. S. Synthesis: 2008; 3707
41. Wen X., Bakali J. E., Deprez-Poulian R., Deprez B. Tetrahedron Lett.: 2012; 53 2440
42. Raghavendra G. M., Ramesha A. B., Revanna C. N., Nandeesh K. N., Mantelingu K., Rangappa K. S. Tetrahedron Lett.: 2011; 52 5571
43. Harrison T., Owens A. P., Sadowski S., Cascieri M. A. Bioorg. Med. Chem. Lett.: 2003; 13 2341
44. Harald B., Gerd B., Udo E. W. L, Helmut M., Thomas P., Bernd S., Werner S., Thomas Z. Synthesis: 2004; 2367
45. Haubner R., Gratius R., Diefenbach B., Goodman S. L., Jonczyk A., Kessler H. J. Am. Chem. Soc.: 1996; 118 7461
46. Dechantsreiter M. A., Planker E., Matha B., Lohof E., Holzeman G., Jonczyk A., Goodman S. L., Kessler H. J. Med. Chem.: 1999; 42 3033
47. Dai X., Su Z., Liu J. O. Tetrahedron Lett.: 2000; 41 6295