Oligosaccharide synthesis on controlled-pore glass as solid phase material

Synlett

Volumn , Issue 2, 1998, Pages 171-173

  Heckel, Alexander ^a   Mross, Elmar ^a   Jung, Karl Heinz ^a   Rademann, Jörg ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002295513     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3127     Document Type: Article

References (33)

1. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. - The helpful discussions with Dr. Rademann, J. are gratefully acknowledged.
2. For a review of early work in this field, see: Fréchet, J.M.J. In Polymer-supported Reactions in Organic Chemistry; Hodge, P.; Sherrington, D.C., Eds.; Chichester, 1980; Chapter 8, p. 407.
3. For more recent chemical glycosylations on solid phase: (a) Rademann, J.; Schmidt, R.R. Tetrahedron Lett. 1996, 37, 3989-3990;
4. J. Org. Chem. 1997, 62, 3650-3653.
5. (b) Randolph, J.T.; Danishefsky, S.J. Angew. Chem. 1994, 106, 1538-1541;
6. Angew. Chem. Int. Ed. Engl. 1994, 33, 1470-1473;
7. Danishefsky, S.J.; McClure, K.F.; Randolph, J.T.; Ruggeri, R.B. Science 1993, 260, 1307-1309.
8. (c) Yan, L.; Taylor, C.M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953-6954;
9. Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W.C.; Kahne, D. Science, 1996, 274, 1520-1522.
10. (d) Hunt, J.A., Roush, W.R. J. Am. Chem. Soc. 1996, 118, 9998-9999.
11. (e) Andinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007-.
12. (f) Veenemann, G.H.; Notermans, S.; Liskamp, R.M.J.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett. 1987, 28, 6695-6698.
13. (g) Nicolaou, K.C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450.
14. (h) Ito, Y.; Kanie, O.; Ogawa, T. Angew. Chem. 1996, 108, 2691-2693;
15. Angew. Chem. Int. Ed. Engl. 1996, 35, 2510-2512
16. Geckeler, K.E.; Wacker, R. Naturwiss. 1996, 83, 498-513.
17. Eby, R.; Schuerch, C. Carbohydr. Res. 1975, 39, 151-155.
18. Veeneman, G.H.; Brugghe, H.F.; van den Elst, H.; van Boom, J.H. Carbohydr. Res. 1990, 195, C1-C4.
19. Halmcomb, R.L.; Huang, H.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 11315-11322;
20. Schuster, M.; Wang, P.; Paulson, J.C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135-1136.
21. Type 332, pore diameter 250 Å, particle size 20-45 μm, Fa. Grace GmbH (in der Hollerecke 1, D-67547 Worms); CPG with a pore diameter of 1500 Å was employed with similar success.
22. Commercially available from Aldrich.
23. Badley, R.; Ford, W. J. Org. Chem. 1989, 54, 5437-5443.
24. Ellman, G.L., Arch. Biochem. Biophys. 1959, 82, 70-77.
25. Reese, C.B.; Stewart, J.M.C.; van Boom, J.H.; de Leeuw, H.P.M.; Nagel, J.; de Rooy, J.F.M. J. Chem. Soc., Perkin Trans. II, 1974, 293-297;
26. Reese, C.B.; Stewart, J.M.C. Tetrahedron Lett. 1968, 4273-4276.
27. Mayer, T.G.; Kratzer, B.; Schmidt, R.R. Angew. Chem. 1994, 106, 2289-2293;
28. Angew. Chem. Int. Ed. Engl. 1994, 33, 2177-2181.
29. 2,3 = 3.1 Hz, H-2), 6.33 (d, 1 H, H-1), 6.87-6.98 and 7.13-7.35 (m, 20 H, 3 Bn, PA), 8.7 (s, 1 H, NH).
30. 2 and dry acetone, 60 mL each. Finally the product was dried in a stream of dry argon and then in vacuo with gentle warming, affording 7 (1.3829 g; ∼ 80%) as a slightly yellowish powder. In order to prevent the contamination of unreacted materials, each glycosylation reaction was usually performed twice, thus increasing the yield to over 95%. Similar results were obtained for the synthesis of 11 and 15.
31. 2 and dry acetone, 40 mL each. After evaporation of the solvent the product is pre-purified by column chromatography. Pure product is finally obtained by HPLC with a silica gel column and hexane/ethyl acetate as eluent.
32. 2 (40 mL) and finally dry acetone (40 mL). Then the product is dried as described, affording 9 (1.2809 g) as a slightly yellow powder; yield: > 90%; MALDI-TOF analysis did not show any phenoxyacetylated material.
33. 2(PA)], 68.9 (C-2c), 68.8 (C-4b), 69.2 (C-6b), 69.9 (C-6c), 70.9 (C-2b), 71.5 (C-6a), 74.0 (C-2a), 74.2 (C-4c), 74.9 (C-4a), 74.9 (C-5c), 77.5 (C-3b), 79.2 (C-3c), 80.3 (C-3a), 95.3 (C-1c), 99.2 (C-1b), 99.9 (C-1a), 114.5-157.6 (Bn, PA).