Synthesis of new poly(ethyleneglycol)s with a high loading capacity

Journal of Organic Chemistry

Volumn 63, Issue 24, 1998, Pages 8628-8629

  Benaglia, Maurizio ^a   Annunziata, Rita ^a   Cinquini, Mauro ^a   Cozzi, Franco ^a   Ressel, Stefano ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

MACROGOL;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0031735591     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981451t     Document Type: Article

References (38)

1. Presented in part by M.B. at the 12th International Congress on Organic Synthesis (ICOS-12), Venice, Italy, June 28-July 2, 1998.
2. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
3. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
4. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
5. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
6. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
7. Reviews: (a) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489. (b) Pillai, V. N. R.; Mutter, M. Acc. Chem. Res. 1981,14, 122. (c) Bonora, G. M. in Seminars in Organic Synthesis; Cozzi, F., Ed.; Societa' Chimica Italiana, Roma, 1998; pp 117-142. For recent reviews on the use of polymeric supports in organic synthesis, see: (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555. (f) Hermkens, P. H. H.; Ottenhejm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527.
8. For a recent discussion of the effects of the polymer structure on the kinetics of solid phase organic reactions, see: Li, W.; Yan, B. J. Org. Chem. 1998, 63, 4092.
9. For instance, by comparing the prices of different polymers functionalized with primary OH groups, and considering the number of functional groups per gram of polymer, PEG polymers cost 10-500 times less than other commercially available polymeric matrixes.
10. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
11. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
12. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
13. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
14. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
15. 5000 and related polymers not included in ref 2, see: (a) Zhu, J.; Hegedus, L. S. J. Org. Chem. 1995, 60, 5831. (b) Park, W. K. K.; Auer, M.; Jaksche, H.; Wong, C. H. J. Am. Chem. Soc. 1996, 118, 10150. (c) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Dreef-Tromp, C. M.; Willems, H. A. N.; Westerduin, P.; van Veelen, P.; van Boeckel, C. A. A. Biorg. Med. Chem. Lett. 1997, 7, 1175. (f) Blettner, C. G.; Konig, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295.
16. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
17. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
18. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
19. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
20. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
21. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
22. For recent immobilization of ligands and reagents on PEG and other soluble polymers not included in refs 2 and 5, see: (a) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632. (b) Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731. (c) Bolm, C.; Gerlach, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 741. (d) Wipf, P.; Venkatraman, S. Tetrahedron Lett. 1996, 37, 4659. (e) Wentworth, P.; Vandersteen, A. M.; Janda, K. D. J. Chem. Soc., Chem. Commun. 1997, 750. (e) Hori, M.; Janda, K. D. J. Org. Chem. 1998, 63, 889. (f) Felder, M.; Giffels, G.; Wandrey, C. Tetrahedron: Asymmetry 1997, 8, 1975.
23. For recent developments of a linker connecting small organic molecules to PEG, see refs 2, 5, 6, and (a) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, 6491. (b) Zhao, X.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977. (c) Zhao, X.; Janda, K. D. Tetrahedron Lett. 1997, 38, 5437. (d) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron 1997, 53, 6645.
24. For recent developments of a linker connecting small organic molecules to PEG, see refs 2, 5, 6, and (a) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, 6491. (b) Zhao, X.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977. (c) Zhao, X.; Janda, K. D. Tetrahedron Lett. 1997, 38, 5437. (d) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron 1997, 53, 6645.
25. For recent developments of a linker connecting small organic molecules to PEG, see refs 2, 5, 6, and (a) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, 6491. (b) Zhao, X.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977. (c) Zhao, X.; Janda, K. D. Tetrahedron Lett. 1997, 38, 5437. (d) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron 1997, 53, 6645.
26. For recent developments of a linker connecting small organic molecules to PEG, see refs 2, 5, 6, and (a) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron Lett. 1996, 37, 6491. (b) Zhao, X.; Jung, K. W.; Janda, K. D. Tetrahedron Lett. 1997, 38, 977. (c) Zhao, X.; Janda, K. D. Tetrahedron Lett. 1997, 38, 5437. (d) Jung, K. W.; Zhao, X.; Janda, K. D. Tetrahedron 1997, 53, 6645.
27. 2α: Chen, S.; Janda, K. D. Tetrahedron Lett. 1998, 39, 3943.
28. (a) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193.
29. (b) Ardoin, N.; Astruc, D. Bull. Soc. Chim. Fr. 1995, 132, 875.
30. (c) Zeng, F.; Zimmermann, S. C. Chem. Rev. 1997, 97, 1681.
31. (d) For a recent example of dendrimer-supported combinatorial chemistry, see: Kim, R. M.; Manna, M.; Hutchins, S. M.; Griffin, P. R.; Yates, N. A.; Bernick, A. M.; Chapman, K. T. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10012.
32. 2O-Ar signal of compounds 3-11, 13, 14 resonates at 4.20 (for compounds 3, 4, 6), 4.16 (5), 4.12 (7), 4.08 (8), 4.15 (9), 4.10 (10, 13), 4.12 (11), 4.13 (14) ppm, respectively.
33. Tetraamine 9 was generally stored as its N-Boc derivative or trifluoroacetate salt and liberated immediately before use.
34. Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937.
35. 5000) and Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253 (on Sasrin).
36. H3/H4 = 4.5 Hz).
37. 13C NMR, IR) in agreement with the proposed structure (see Supporting Information).
38. 5000.