Application of a ring closing metathesis based linker to the solid phase synthesis of oligosaccharides

Synlett

Volumn , Issue 11, 1999, Pages 1802-1804

  Knerr, Laurent ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Linker; Oligosaccharides; Ring closure metathesis; Solid phase synthesis

Indexed keywords

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CHEMICAL REACTION; SOLID STATE;

EID: 0032706852     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2930     Document Type: Article

References (30)

1. For a recent review on polymer supported syntheses of oligosaccharides and glycopeptides see: Osborn, H. M. I.; Tariq, H. K. Tetrahedron 1999, 55, 1807.
2. For applications on Merrifield resin see: (a) Rademann, J.; Geyer, A.; Schmidt, R. R. Angew. Chem. 1998, 110, 1309; Angew. Chem. Int. Ed. Engl. 1998, 37, 1241.
3. For applications on Merrifield resin see: (a) Rademann, J.; Geyer, A.; Schmidt, R. R. Angew. Chem. 1998, 110, 1309; Angew. Chem. Int. Ed. Engl. 1998, 37, 1241.
4. (b) Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
5. (c) Rademann, J.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 3989.
6. For an application on CPG see: Heckel, A.; Mross, E.; Jung, K. H.; Rademann, J.; Schmidt, R. R. Synlett 1998, 171.
7. For some recent applications on different solid supports see: (a) Wang, Z. H.; Douglas, S. P.; Krepinsky, J. I. Tetrahedron Lett. 1996, 37, 6985.
8. (b) Shimizu, H.; Ito, Y.; Kanie, O.; Ogawa, T. Bioorg. Med. Chem. Lett. 1996, 6, 2841.
9. (c) Fukase, K.; Nakai, Y.; Egusa, K.; Porco, Jr., J. A.; Kusumoto, S. Synlett, 1999, 1074.
10. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179; Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
11. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179; Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
12. For recent general reviews on the metathesis reaction see; (a) Chang, S.; Grubbs, R. H. Tetrahedron 1998, 54, 4413.
13. (b) Schuster, M.; Blechert, S. Angew. Chem., 1997, 109, 2124; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036.
14. (b) Schuster, M.; Blechert, S. Angew. Chem., 1997, 109, 2124; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036.
15. For reviews on applications of ring closing metathesis see: (a) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
16. (b) Schmalz, H. G. Angew. Chem. 1995, 107, 1981; Angew. Chem. Int. Ed. 1995, 34, 1833.
17. (b) Schmalz, H. G. Angew. Chem. 1995, 107, 1981; Angew. Chem. Int. Ed. 1995, 34, 1833.
18. For some recent RCM mediated cyclization/cleavage strategies leading to cyclic alkenes see: (a) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268.
19. (b) Pernerstorfer, J.; Schuster, M.; Blechert, S. J. Chem. Soc., Chem. Commun. 1997, 1949.
20. (c) Veerman, J. J. N.; van Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 1998, 2583.
21. (d) Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron 1999, 55, 8189.
22. Peters, J. ; Blechert, S. Synlett 1997, 348.
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24. Krapcho, P. A.; Glynn, G. A.; Grenon, B. J. Tetrahedron Lett. 1967, 3, 215.
25. Knerr, L.; Schmidt, R. R. unpublished results.
26. Lay, L.; Windmüller, R. ; Reinhardt, S.; Schmidt, R. R. Carbohydr. Res. 1997, 303, 39.
27. 2. After extensive drying under high vacuum the resin was glycosylated a second time (1.7 eq. 11, 0.1 eq. TMSOTf) to ensure a complete reaction.
28. 2. The combined filtrates were evaporated. The resin was dried for 18h under high vacuum and submitted a second time to the cleavage conditions. The combined filtrates of both cleavage reactions were then submitted to silica gel column chromatography to afford 37 mg of 13 (51% from 7).
29. 2 were degassed. A few crystals of 1 were added to this suspension. The mixture was stirred for 4h at r.t.. Satisfactory TLCs are obtained from the crude reaction. The catalyst was then filtered over a small pad of silica gel (0.4*1cm) and the cleaved compounds were eluted with ethyl acetate (10 ml). The solvents were then evaporated and the resulting crude was analyzed by Maldi-TOF in the usual way.
30. 2].