Polymer-Supported Oligosaccharides via n-Pentenyl Glycosides: Methodology for a Carbohydrate Library

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5660-5661

  Rodebaugh, Robert ^a   Joshi, Subodh ^a,b   Fraser Reid, Bert ^b   Geysen, H Mario ^c  

^a DUKE UNIVERSITY   (United States)

^b Natural Products and Glycotechnology Research Institute Inc   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000355521     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970216s     Document Type: Article

References (32)

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5. For a review of early work see: Malik, H.; Bauer, H.; Tschakert, J.; Voelter, W. Chem.-Ztg. 1990, 114, 371. (b) Frechet, J. M. J. Polymer-Supported Reactions in Organic Synthesis; Eby, R., Schuerch, C., Eds.; Wiley: New Yor, 1980; Chapt. 8. (c) Krepinsky, J. S.; Douglas, S. P.; Whitfield, D. M. Synth. Polym. 1994, 242, 280.
6. For a review of early work see: Malik, H.; Bauer, H.; Tschakert, J.; Voelter, W. Chem.-Ztg. 1990, 114, 371. (b) Frechet, J. M. J. Polymer-Supported Reactions in Organic Synthesis; Eby, R., Schuerch, C., Eds.; Wiley: New Yor, 1980; Chapt. 8. (c) Krepinsky, J. S.; Douglas, S. P.; Whitfield, D. M. Synth. Polym. 1994, 242, 280.
7. For a review of early work see: Malik, H.; Bauer, H.; Tschakert, J.; Voelter, W. Chem.-Ztg. 1990, 114, 371. (b) Frechet, J. M. J. Polymer-Supported Reactions in Organic Synthesis; Eby, R., Schuerch, C., Eds.; Wiley: New Yor, 1980; Chapt. 8. (c) Krepinsky, J. S.; Douglas, S. P.; Whitfield, D. M. Synth. Polym. 1994, 242, 280.
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14. See for example, Borchardt, A.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 373.
15. 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. E. Science 1996, 274, 1520.
16. Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; R. Merritt, Rao, C. S., Roberts, C.; Madsen, R. Synlett 1992, 927. Madsen, R.; Fraser-Reid, B. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Lausanne, Switzerland, 1995; Chapter 4.
17. Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; R. Merritt, Rao, C. S., Roberts, C.; Madsen, R. Synlett 1992, 927. Madsen, R.; Fraser-Reid, B. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Lausanne, Switzerland, 1995; Chapter 4.
18. Brown, B. B.; Wagner, D. S.; Geysen, H. M. Mol. Diversity 1995, 1, 4.
19. Merrifield resin loading = 1 mmol/g (purchased from Aldrich). Glycosidations were carried out at room temperature using 4 equiv of NPG donor. Reaction yields were judged by weight gain of resin, elemental analysis for nitrogen, and HPLC analysis of methyl benzoate from treatment with NaOMe/MeOH in THF.
20. Giralt, E.; Rizo, J.; Pedroso, E. Tetrahedron 1984, 40, 4141.
21. Fraser-Reid, B.; Konradsson, P.; Mootoo, D. R.; Udodong, U. J. Chem. Soc., Chem. Commun. 1988, 823.
22. Frechet, J. M.; Schuerch, C. J. Am. Chem. Soc. 1972, 94, 604.
23. Yield range was 76-100%. Most couplings proceeded with an average yield of >90%.
24. 15 This technique could not be applied to the larger trisaccharide 8, and so the new anomeric center in 8 was assigned by analogy.
25. Merritt, J. R.; Fraser-Reid, B. Unpublished results.
26. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155.
27. Rodebaugh, R.; Debenham, J. S.; Fraser-Reid, B. J. Carbohydr. Chem., in press.
28. 5
29. The 1 → 4 disaccharide, however, was not obtained during these studies. Obviously, the C4-OH of the pertinent benzoylated acceptor is inactivated by steric hindrance and electronic withdrawal.
30. Chiron Mimotopes, 11055 Roselle St., San Diego, CA 92121. Catalog no. 12.48, Batch no. 491-1. Loading = 1.6 μmol per crown.
31. Rich, D. H.; Gurwara, S. K. J. Am. Chem. Soc. 1975, 97, 1575.
32. All compounds exhibited satisfactory spectral data. Yields from resin reactions refer to isolated product.