The first polymer-assisted solution-phase synthesis of deoxyglycosides

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3623-3626

  Kirschning, Andreas ^a   Jesberger, Martin ^b   Schönberger, Andreas ^b  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOSIDE; POLYMER; TESTOSTERONE; TRISACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; GLYCOSYLATION; MOLECULAR GENETICS; SYNTHESIS;

CARBOHYDRATE SEQUENCE; GLYCOSIDES; GLYCOSYLATION; INDICATORS AND REAGENTS; MOLECULAR SEQUENCE DATA; POLYMERS; TESTOSTERONE; TRISACCHARIDES;

EID: 0035891757     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016545v     Document Type: Article

References (49)

1. (a) Kirschning, A.; Bechthold, A.; Rohr, J. Top. Curr. Chem. 1997, 188, 1-88.
2. (b) Kennedy, J. F., White, C. A. Bioactive Carbohydrates in Chemistry, Biochemistry, and Biology; Ellis Horwood: Chichester, 1983.
3. (c) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482-1522; Angew. Chem., Int. Ed. Engl. 1996, 35, 1380-1419.
4. (c) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482-1522; Angew. Chem., Int. Ed. Engl. 1996, 35, 1380-1419.
5. For example, modifying the aminodeoxy sugar vancosamine as a constituent of the antibiotic vancomycin can dramatically increase the activity against vancomycin-resistant strains: Malabarba, A.; Nicas, T. I.; Thompson, R. C. Med. Res. Rev. 1997, 17, 69-173.
6. Jesberger, M.; Jaunzems, J.; Jung, A.; Jas, G.; Schönberger, A.; Kirschning, A. Synlett 2000, 1289-1293.
7. (b) Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998-9999.
8. Reviews: (a) Polymers as Aids in Organic Chemistry; Mathur, N. K., Narang, C. K., Williams, R. E., Eds.; Academic Press: New York, 1980; pp 105-116.
9. (b) Kahne, D. Curr. Opin. Chem. Biol. 1997, 1, 130-135.
10. (c) Danishefsky, S. J.; Roberge, J. Y. Glycopept. Relat. Compd. 1997, 245-294.
11. (d) Sofia, M. J. Mol. Div. 1998, 3, 75-94.
12. (e) Schweizer, F.; Hindsgaul, O. Curr. Opin. Chem. Biol. 1999, 3, 291-298.
13. (f) Osborn, H. M. I.; Khan, T. H. Tetrahedron 1999, 55, 1807-1850.
14. (g) St. Hilaire, P. M.; Meldal, M. Angew. Chem. 2000, 112, 1210-1228; Angew. Chem., Int. Ed. 2000, 39, 1162-1179.
15. (g) St. Hilaire, P. M.; Meldal, M. Angew. Chem. 2000, 112, 1210-1228; Angew. Chem., Int. Ed. 2000, 39, 1162-1179.
16. Recent reviews on polymer-supported reagents: (a) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem.. Int. Ed. 2001, 40, 650-679.
17. (b) Kirschning, A.; Monenschein, H.; Wittenberg, R. Chem Eur. J. 2000, 6, 4445-4450.
18. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J., J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
19. (d) Drewry, D. H.; Coe, D. M.; Poon, S. Med. Res. Rev. 1999, 19, 97-148.
20. (a) Sourkouni-Argirusi, G.; Kirschning, A. Org. Lett. 2001, 2, 3781-3784.
21. (b) Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722: Angew. Chem., Int. Ed. 1999, 38, 2594-2596.
22. (b) Kirschning, A.; Monenschein, H.; Schmeck, C. Angew. Chem. 1999, 111, 2720-2722: Angew. Chem., Int. Ed. 1999, 38, 2594-2596.
23. Monenschein, H.; Sourkouni-Argirusi, G.; Schubothe, K. M.; O'Hare, T.; Kirschning, A. Org. Lett. 1999, 1, 2101-2104.
24. Kirschning, A.; Jesberger, M.; Monenschein, H. Tetrahedron Lett. 1999, 40, 8999-9002.
25. (a) Roush, W. R.; Briner, K.; Sebesta, D. P. Synlett 1993, 264-266.
26. (b) Kosma, P.; Sekljic, H.; Balint, G. J. Carbohydr. Chem. 1996, 15, 701-714.
27. (c) Lafont, D.; Boullanger, P.; Carvalho, F.; Vottero, P. Carbohydr. Res. 1997, 297, 117-126.
28. (d) Lafont, D.; Boullanger, P.; Rosenzweig, M. J. Carbohydr. Chem. 1998, 17, 1377-1393.
29. (e) Kirschning, A.; Plumeier, C., Rose, L. J. Chem. Soc., Chem. Commun. 1998, 33-34.
30. (f) Roush, W. R.; Bennett, C. E. J. Am. Chem. Soc. 1999, 121, 3541-3542.
31. (g) Roush, W. R.; Gung, B. W.; Bennett, C. E. Org. Lett. 1999, 1, 891-893.
32. (h) Roush, W. R.; Narayan, S.; Bennett, C. E.; Briner, K. Org. Lett. 1999, 1, 895-897.
33. (i) Roush, W. R.; Narayan, S. Org. Lett. 1999, 1, 899-902.
34. (a) Olah, G. A.; Mehrotra, A. K., Synthesis 1982, 962-962.
35. (b) Olah, G. A.; Iyer, P. S.; Prakash, G. K. S. Synthesis 1986, 513-531.
36. Toshima, K.; Nagai, H.; Matsumura, S. Synlett 1999, 1420-1422.
37. Jyoima, T.; Miyamoto, N.; Ogawa, Y.; Matsumura, S.; Toshima, K. Tetrahedron Lett. 1999, 40, 5023-5026.
38. (b) Florent, J.-C.; Monneret, C. J. Chem. Soc., Chem. Commun. 1987, 1171-1172.
39. (c) Laszlo, P. Science 1987, 235, 1473-1477.
40. (d) Sieskind, O.; Albrecht, P. Tetrahedron Lett. 1993, 34, 1197-1200.
41. Smith, E. M. Tetrahedron Lett. 1999, 40, 3285-3288.
42. In some cases, oligo-and polymeric impurities originated from the resins were present in the crude product as judged by 1H NMR analysis. Under these circumstances, a simple gel-filtration step became necessary for obtaining analytically pure samples.
43. (a) Krohn, K.; Rohr, J. Top. Curr. Chem. 1997, 188, 127-205.
44. (b) Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 9, 103-137.
45. Kirschning, A. J. Prak. Chem. 2000, 342, 508-511.
46. (a) Delmond, B.; Dumartin, G. In Solid State Organometallic Chemistry: Methods and Applications: Gielen, M., Willem, R., Wrackmeyer, B., Eds.; Wiley: Chichester, 1999; pp 445-471.
47. (b) Gerigk, U.; Gerlach, M.; Neumann, W. P.; Vieler, R.; Weintritt, V. Synthesis 1990, 448-452.
48. (c) Neumann, W. P.; Peterseim, M. React. Polym. 1993, 20, 189-205.
49. - form) was employed for the treatment of various silyl ethers. While both primary and secondary triethylsilyl groups can rapidly be removed, this polymer-bound reagent is not reliable when cleaving secondary primary TBS ethers.