The prop-2-ynyloxy carbonyl function (POC): A new amino-protecting group removable from sulfur-containing peptides by ultrasonic irradiation with tetrathiomolybdate under mild and neutral conditions

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 771-774

  Sinha, Surajit ^a   Ilankumaran, Palanichamy ^a   Chandrasekaran, Srinivasan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Amino acids and derivatives; Protecting groups

Indexed keywords

AMINO ACID DERIVATIVE;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ULTRASOUND;

EID: 0033593498     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02408-3     Document Type: Article

References (21)

1. (a) M. Bergmann, L. Zervas, Ber. Dtsch. Chem. Ges., 1932, 65, 1192;
2. (b), F. C. McKay, N. F. Albertson, J. Am. Chem. Soc., 1957, 79, 4686;
3. (c) G. W. Anderson, A. C. McGregor, J. Am. Chem. Soc., 1957, 79, 6180;
4. (d) G. W. Anderson, F. M. Callahan, J. Am. Chem. Soc., 1960, 82, 3359;
5. (e) E. Vedejs, S. Lin, A. Klapars, J. Wang, J. Am. Chem. Soc., 1996, 118, 9796.
6. L. A. Carpino, G. Y. Han, J. Am. Chem. Soc., 1970, 92, 5748.
7. E. A. Babiker, M. A. Gattadahalli., P. R..Garfield, E. M. Gary, J. Org. Chem., 1979, 44, 3442.
8. P. Ilankumaran, N. Manoj, S. Chandrasekaran, Chem. Commun., 1996, 1957.
9. Z. Wimmer, D. Saman, V. Nemec, W. Francke, Helv. Chim. Acta., 1994, 77, 561.
10. 2 and diethylether (1:5, 30×5, 150 mL), the solvent removed under reduced pressure, and the crude product purified by chromatography on silica gel.
11. H. Vorbruggen, K. Krolikiewicz, Angew. Chem; Int. Ed. Engl., 1975, 14, 818.
12. J. Goodacre, R. J. Ponsford, I. Stirling, Tetrahedron Lett., 1975, 3609.
13. (a) D.R. Taylor, Chem. Rev., 1967, 67, 317;
14. (b) J. K. Crandall, D. J. Keyton, J. Kohne, J. Org. Chem.., 1968, 33, 3655;
15. (c) A. Claesson, L. I. Olsson, J. Am. Chem. Soc., 1979, 101, 7302;
16. P. H. Dixneuf, T. Guyot, M. D. Ness, S. M. Roberts, Chem. Commun., 1997, 2083.
17. 3CN) under the same condition was recovered unchanged.
18. (a) G. L. Southard, B. R. Zaborowsky, J. M. Pette, J. Am. Chem. Soc., 1971, 93, 3302;
19. (b) L. A. Carpino, K. N. Parameswaran, R. K. Kirkley, J. W. Spiewak, E. Schmitz, J. Org. Chem., 1970, 35, 3291.
20. 2 (1 atm) for 24 h turned out to be unsatisfactory with a number of products ensuing.
21. + ] (0.4), 486 (2.8), 430 (1.5), 395 (2.8), 339 (2.8), 91 (100).