1,1-Dioxonaphtho[1,2-b]thiophene-2-methyloxycarbonyl (α-Nsmoc) and 3,3-dioxonaphtho[2,1-b]thiophene-2-methyloxycarbonyl (β-Nsmoc) amino-protecting groups

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1729-1736

  Carpino, Louis A ^a   Abdel Maksoud, Adel Ali ^a,b   Ionescu, Dumitru ^a,c   Mansour, E M E ^a,d   Zewail, Mohamed A ^a,e  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b GENETIC ENGINEERING AND BIOTECHNOLOGY RESEARCH INSTITUTE   (Egypt)

^c UNIVERSITY OF BUCHAREST   (Romania)

^d Alexandria University Faculty Of Science   (Egypt)

^e NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

BSMOC RESIDUES; MICHAEL ADDITION; NAPHTHOTHIOPHENE;

ALCOHOLS; ALDEHYDES; DERIVATIVES; OLEFINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINO ACIDS;

1,1 DIOXONAPHTHO[1,2 B]THIOPHENE 2 METHYLOXYCARBONYL DERIVATIVE; 3,3 DIOXONAPHTHO[2,1 B]THIOPHENE 2 METHYLOXYCARBONYL DERIVATIVE; CARBONYL DERIVATIVE; PIPERIDINE DERIVATIVE; SULFONE DERIVATIVE; TETRALIN DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICHAEL ADDITION; PEPTIDE ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS;

ALCOHOLS; AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; PIPERIDINES; THIOPHENES;

EID: 33847651271     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062397g     Document Type: Article

References (24)

1. Carpino, L. A.; Ismail, M.; Truran, G. A.; Mansour, E. M. E.; Iguchi, S.; Ionescu, D.; El-Faham, A.; Riemer, C.; Warrass, R. J. Org. Chem. 1999, 64, 4324.
2. Carpino, L. A. Acc. Chem. Res. 1987, 20, 401.
3. For the use of exactly 1 equiv of a secondary amine (4- piperidinopiperidine) to deblock a sensitive Bsmoc paclitaxel derivative, see: Greenwald, R. B.; Zhao, H.; Reddy, P. J. Org. Chem. 2003, 68, 4894.
4. (a) Carpino, L. A.; Philbin, M.; Ismail, M.; Truran, G. A.; Mansour, E. M. E.; Iguchi, S.; Ionescu, D.; El-Faham, A.; Riemer, C.; Warrass, R.; Weiss, M. S. J. Am. Chem. Soc. 1997, 119, 9915.
5. (b) Carpino, L. A.; Krause, E.; Sferdean, C. D.; Schumann, M.; Fabian, H.; Bienen, M.; Beyermann, M. Tetrahedron Lett. 2004, 45, 7519.
6. (a) Carpino, L. A.; Philbin, M. J. Org. Chem. 1999, 64, 4315.
7. (b) McDowell, S. T.; Stirling, C.J.M. J. Chem. Soc. B 1967, 343.
8. (c) McDowell, S. T.; Stirling, C.J.M. J. Chem. Soc. C 1967, 351.
9. Tedjamulia, M. L.; Tominaga, Y.; Castle, R. N.; Lee, M. L. J. Heterocycl. Chem. 1983, 20, 1143.
10. Clarke, K.; Gregory, D. N.; Scrowston, R. M. J. Chem. Soc., Perkin Trans, 1 1973, 2956.
11. McKillip, A.; Kemp, D. Tetrahedron 1989, 45, 3299.
12. Campaigne, E.; Cline, R. E. J. Org. Chem. 1956, 21, 32 and 39.
13. Bolin, D. R.; Sytwu, I.-I.; Humiec, F.; Meienhofer, J. Int. J. Pept. Protein Res. 1989, 33, 353.
14. Carpino, L. A.; Sadat-Aalaee, D.; Chao, H. G.; DeSeims, R. H. J. Am. Chem. Soc. 1990, 112, 9651.
15. A similar course for the Bsmoc deblocking process was previously recorded. See the Supporting Information of ref 4a, page S13.
16. (a) Carpino, L. A.; Chao, H. G.; Tien, J.-H. J. Org. Chem. 1989, 54, 4302.
17. (b) Carpino, L. A.; Gao, H.-S.; Ti, G.-S.; Segev, D. J. Org. Chem. 1989, 54, 5887.
18. (c) Carpino, L. A.; Cohen, B. J.; Lin, Y-Z.; Stephens, K. E., Jr.; Triolo, S. A. J. Org. Chem. 1990, 55, 251.
19. (a) Arshady, R.; Atherton, E.; Clive, D. L. J.; Sheppard, R. C. J. Chem. Soc., Perkin Trans. I 1981, 529.
20. (b) Schnölzer, M.; Jones, A.; Alewood, P. F.; Kent, S. B. H. Anal. Biochem. 1992, 204, 335.
21. (c) Carpino, L. A.; El-Faham, A.: Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201.
22. Gilchrist, T. L.; Summersell, R. J. J. Chem. Soc:, Perkin Trans. I 1988, 2595.
23. Paquet, A. Can. J. Chem. 1982, 60, 976.
24. For a general description of the syringe methodology, see ref 1.