(9H-fluoren-9-yl)methanesuIfonyl (Fms): An amino protecting group complementary to Fmoc

European Journal of Organic Chemistry

Volumn , Issue 22, 2010, Pages 4201-4204

  Ishibashi, Yoshitaka ^a   Miyata, Kengo ^a   Kitamura, Masato ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Peptides; Phosphorus; Protecting groups; Sulfonamides

Indexed keywords

EID: 77954967035     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000682     Document Type: Article

References (34)

1. a) L. A. Carpino, G. Y. Han, J. Am. Chem. Soc. 1970, 92, 5748-5749
2. b) L. A. Carpino, G. Y. Han, J. Org. Chem, 1972, 37, 3404-3409
3. c) for a review, see: G. B. Fields, R. L. Noble, Int. J. Peptide Protein Res. 1990, 35, 161-214
4. d) for an Fmoc compatible Nsc PG [2-(4-nitrophenylsulfonyl) ethoxycarbonyl], see: A. Isidro-Llobet, M. Alvarez, F. Albericio, Chem. Rev. 2009, 109, 2455-2504.
5. P. G. M. Wuts, T. W. Greene, Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, New Jersey, 2006, pp. 711-713.
6. a) A. Paquet, F. M. F. Chen, N. L. Benoiton, Can. J. Chem. 1984, 62, 1335-1338
7. b) L. A. Carpino, H. G. Chao, M. Beyermann, M. Bienert, J. Org. Chem, 1991, 56, 2635-2642
8. c) D. S. Perlow, I M. Erb, N. P. Gould, R. D. Tung, R. M. Freidinger, P. D. Williams, D. F. Veber, J. Org. Chem, 1992, 57, 4394-4400
9. d) J. Coste, E. FréBrot. P. Jouin, J. Org. Chem. 1994, 59, 2437-2446
10. e) K. Akaji, N. Kuriyama, Y. Kiso, J. Org. Chem. 1996, 61, 3350-3357.
11. a) R. Kluger, J. L. W. Chan, J. Am, Chem. Soc. 1976, 98, 4913-4917
12. b) N. E. Jacobsen, P. A. Bartlett, J. Am. Chem. Soc. 1983, 105, 1613-1619
13. c) L. A. Reiter, B. P. Jones, J. Org. Chem, 1997, 62, 2808-2812
14. d) M. Nasopoulou, M. Matziari, V. Dive, A. Yiotakis, J. Org. Chem, 2006, 71, 9525-9527.
15. 3 hybridization, resulting in higher aromatic character and in a smaller N-S rotation barrier.
16. For details see the Supporting Information.
17. [1]
18. α-Amino carboxylic acid abbreviation follows the IUPAC rule. The TV-PG and ester PG are denoted as a prefix and a suffix, respectively. α-Amino phosphonic acid is denoted by the addition of "P" at the end of the three-letter abbreviation, e.g., H-AIaP(OH)-OH for 1.-aminoethylphosphonic acid.
19. a) E. Atherton, C Bury, R. C Sheppard, B. J. Williams, Tetrahedron Lett. 1979, 20, 3041-3042
20. b) J. Martinez, J. C. Tolle, M. Bodanszky, J. Org. Chem. 1979, 44, 3596-3598
21. c) for Fmoc removal using Pd/C, see: H. Sajiki, T. Maegawa, K. Hirota, Jpn. Kokai Tokkyo Koho Jpn. Pat. 8887, 2007.
22. J. Brinckmann, H. Notbohm, P.K. Müller (Eds.), Collagen Primer in Structure, Processing and Assembly Series: Topics in Current Chemistry, Springer, New York, 2005.
23. Y. Ishibashi, M. Kitamura, Chem. Commun. 2009, 6985-6987.
24. This value is highly consistent with that reported for related compounds. See: R. Hirschmann, K. M. Yager, C. M. Taylor, W. Moore, P. A. Sprengeler, J. Witherington, B. W. Phillips, A.B. Smith, J. Am. Chem. Soc. 1995, 117, 6370-6371. Compound 11 could not be isolated by silica gel column chromatography of the crude mixture. This may be due to the moisture instability of 11. See,
25. O. V. Korenchenko, A. Y. Aksinenko, V. B. Sokolov, I. V. Martynov, Heteroat. Chem. 1992, 3, 147-150.
26. a) Nosyl: T. Fukuyama, C-K. Jow, M. Cheung, Tetrahedron Lett. 1995, 36, 6373-6374
27. b) dinitrobenzensulfonyl: T. Fukuyama, M. Cheung, C.-K. Jow, Y. Hidai, T. Kan, Tetrahedron Lett. 1997, 38, 5831-5834
28. c) SES: S. M. Weinreb, D.M. Demko, T. A. Lessen, I P. Demers, Tetrahedron Lett. 1986, 27, 2099-2102.
29. a) V.P. Kukhar, H. R. Hudson (Eds.), Aminophosphonic and Aminophosphinic Acids, Wiley-VCH, Weinheim, Germany, 2000
30. b) P. Kafarski, B. Lejczak, Phosphorus Sulfur Silicon Relut, Elem. 1991, 63, 193-215
31. c) see also: A. Peyman, E. Uhlmann, K. Wagner, S. Augustin, G. Breipohl, D. W. Will, A. Schäfer, H. Wallmeier, Angew. Chem. Int. Ed. Engl 1996, 35, 2636-2638
32. d) A. Peyman, E. Uhlmann, G. Breipohl, H. Wallmeier (Hoechst AG), EP 0739898A2, 1996
33. e) A. C. van der Laan, R. Stromberg, I H. van Boom, E. Kuyl-Yeheskiely, V. A. Efimov, O. G. Chakhmakhcheva, Tetrahedron Lett. 1996, 37, 7857-7860.
34. Other carbamate-type PGs such as Nsc having a high interchangeablity with. Fmoc could be extended to the corresponding sulfonamide-based PGs in a similar way to the present chemistry.