Solid-phase synthesis of levoglucosan derivatives

Synlett

Volumn , Issue 10, 1998, Pages 1085-1090

  Brill, Wolfgang K D ^a   De Mesmaeker, Alain ^a   Wendeborn, Sebastian ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001921146     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1874     Document Type: Article

References (35)

1. For example: a) Takatori, K.; Kajiwara, M. Synlett 1995, 280-282;
2. b) Ichikawa, Y.; Mondan, R.; Kuzuhara, H. Tetrahedron Lett. 1986, 27, 611-614;
3. c) Frazer-Reid, B.; Magdzinski, L.; Molino, B. J. Am. Chem. Soc. 1984, 106, 731-734;
4. d) Ogawaj T.; Kawano, T.; Matsui, M. Carbohydrate Research 1977, 57, C31-35;
5. e) Sviridov, A. F.; Ermolenko, N. S.; Yashunsky, D. V.; Borodkin, V. S.; Kochetkov, N. K. Tetrahedron Lett. 1987, 28, 3835-3838.
6. For example: Paulsen, H.; Schüller, M. Liebigs Ann. Chem. 1987, 249-258.
7. For instance: a) Kriecheldorf, H. R.; Delius, U. Makromol. Chem. 1989, 190, 1289-1301;
8. b) Gorkovenko, A. A.; Berman, E. L.; Ponomarenko, V. A. Bioorg. Khim. 1987, 13, 218-222; (English translation: 126-129);
9. c) Uryu, T.; Hatanaka, K.; Matsuzaki, K.; Kuzuhara, H. Macromolecules 1983, 16, 853-858.
10. a) Cerny, M.; Gut, V.; Pacak, J. Collect. Czech, Chem. Commun. 1961, 26, 2542-2550;
11. b) Szeja, W. Carbohydrate Res. 1988, 183, 135-139;
12. Cerney, M.; Stanek Jr., J.; Pacak, J. Collect. Czech. Chem. Commun. 1969, 34, 849-856.
13. For review: Cerny, M. Levoglucosanone and Levoglucosanes, Chemistry and Applications, Witczak, Z. J. (ed.). ATL PRESS 1994, 121-146.
14. Caprino, L. A.; El-Faham, A. J. Org. Chem. 1995, 60, 3561-3564.
15. All described reactions were performed in a glass "frit reactor". Its top was closed by a rubber septum, connected to an Ar-balloon. The bottom contained a P3-glass frit, leading to a narrow outlet, which could either be sealed by a small septum or rubber stopper or fastened tightly onto a PTFE valve to perform washing procedures. This "frit reactor", could be placed in a heating block, mounted on an orbital shaker to allow agitation of the resin during the reactions. Washings were performed in a "flow through" manner when the reactor was mounted on a PTFE valve.
16. 2Cl 1/4(V/ V) for 2min. each. To the combined cleavage solutions were added 1/4 volume eq. of toluene prior to evaporation in vacuo (T>40°C).
17. CH=147Hz C2 (sugar).
18. a) Schwesinger, R.; Schlemper, H. Angew. Chem. 1987, 99, 1212-1214;
19. Angew. Chem. Int. Ed. Engl. 1987, 26, 1167-1168 ;
20. b) Esswein, B.; Steidel, N. M.; Moeller, M. Macromol. Rapid Commun. 1996, 17, 143-148;
21. c) Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E. M.; Peters, K.; von Schnering, H. G. Angew. Chem. 1993, 105, 1420-1422;
22. Angew. Chem. Int. Ed. Engl. 1993, 32, 1361-1363.
23. RAM-resin is produced by Rapp Polymere GmbH, Ernst-Simon-Str. 9, D-72072 Tübingen, Germany.
24. Chini, M.; Crotti, P.; Maccia, F. Tetrahedron Lett. 1990, 32, 4661-4664.
25. 3/2,6-lutidine 1/4 (V/V), 100°C, sealed tube.
26. 6 (2eq.),0.2M thiol (10eq.), 2,6-lutidine/DBU 9/1(V/ V), 100°C, 16h.
27. Kataoka, S.; Imai, J.; Yamaji, N.; Kato, M.; Kawada, T.; Imai, S. Chem. Pharm. Bull. 1990, 38, 1596-1600.
28. 3: 7.14, 7.65, 7.68 (iodobenzyl).
29. Gaffney, B. L.; Marki, L. A.; Jones, R. A. Tetrahedron 1984, 40, 3-13.
30. a) Wellow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034-5037,
31. b) Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc. Chem. Commun. 1994, 2395.
32. Hodgson, D. M.; Witherington, J.; Moloney, B. A.; Richards, I. C.; Brayer, J.-L. Synlett 1995, 32-34.
33. Fancelli, D.; Fagnola, M. C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311-2314.
34. 5: 3.79, 4.22, 4.35, 6.93, 7.45.
35. Multiple couplings: After a coupling reaction as under ref. 21. the resin is washed 10x with oxygen-free dioxane and is subsequently subjected with the reagents for a subsequent coupling reaction.