Suzuki cross-coupling of carbohydrates: Synthesis of β-arylmethyl-C-glycosides and aryl-scaffolded trisaccharide mimics

Synlett

Volumn , Issue 12, 1997, Pages 1406-1408

  Johnson, Carl R ^a   Johns, Brian A ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002412759     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0030-1260180     Document Type: Article

References (35)

1. (a) Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Ann. Rev. Biochem. 1988, 57, 785.
2. (b) Varki, A. Glycobiology 1993, 3, 97.
3. (c) Dwek, R. A. Chem. Rev. 1996, 96, 683.
4. (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton. FL, 1995.
5. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Elsevier Science: Oxford, 1995.
6. (c) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
7. (d) Bertozzi, C.; Bednarski, M. "Synthesis of C-Glycosides; Stable Mimics of O-Glycosidic Linkages" in Modern Methods in Carbohydrate Synthesis, Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic: Amsterdam, 1996; Chapter 14.
8. For detailed discussions and data on the topic of C vs. O glycoside similarities and differences see (a) Duda, C. A.; Stevens, E. S. J. Am. Chem. Soc. 1993, 115, 8487.
9. (b) Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88.
10. (c) Espinosa, J, -F; Cañada, J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
11. For discussions of previous syntheses and biology of arylmethyl-C-glycosides see (a) Dubois, E.; Beau, J. -M.; J. Chem. Soc. Chem. Commun. 1990, 1191.
12. (b) Dubois, E.; Beau, J.-M.; Carbohydr. Res. 1992, 228, 103.
13. (c) Schmidt, R. R.; Dietrich, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 1328.
14. (d) Panigot, M. J.; Curley Jr., R. W. J. Carbohydr. Chem. 1994, 13, 293.
15. (e) Panigot, M. J.; Humphries, K. A.; Curley Jr., R. W. J. Carbohydr. Chem. 1994, 13, 303.
16. (a) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
17. (b) Suzuki, A. Pure Appl. Chem. 1991, 63, 419.
18. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
19. (d) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856.
20. (a) 2,3,4,6-Tetra-O-benzyl-D-glucose in available from Sigma Chemical Co.
21. (b) 2,3,4,6-Tetra-O-benzyl-D-mannose was prepared according to Koto, S.; Morishima, N.; Miyata, Y.; Zen, S. Bull. Chem. Soc. Jpn. 1976, 49, 2639.
22. (a) Rajanbabu, T. V.; Reddy, G. S. J. Org. Chem. 1986, 51, 5458.
23. (b) Hanessian, S.; Ugolini, A. Carbohydr. Res. 1984, 130, 261.
24. (a) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
25. (b) Csuk, R.; Glänzer, B. I. Tetrahedron 1991, 47, 1655.
26. 3) δ 37.9, 68.9, 73.4, 75.0, 75.2, 75.6, 78.6, 79.0, 80.0, 81.8, 87.4, 126.1, 127.5, 127.6, 127.7, 127.8, 127.9, 128.1, 128.3, 128.4, 128.5, 128.6, 129.7, 138.1, 138.2, 138.4, 138.6, 138.9
27. (a) Juaristi, E.; Cuevas, G. The Anomeric Effect, ; CRC Press: Boca Raton. FL, 1995.
28. (b) "The Anomeric Effect and Associated Stereoelectronic Effects"; Thatcher, G. R. J., Ed.; American Chemical Society: Washington, D.C., 1992; ACS Symp. Ser. No 539.
29. 3) δ 20.6, 20.6, 20.7, 37.9, 62.3, 68.7, 72.0, 74.4, 75.5, 78.3, 126.5, 128.2, 129.4, 137.1, 169.5, 169.7, 170.4, 170.7.
30. 3OD) δ 38.9, 63.2, 72.1, 75.1, 80.1, 81.5, 81.9, 127.1, 129.1, 130.9, 140.5.
31. For discussions of scaffolded oligosaccharide mimics see (a) Patch, R. J.; Chen, H.; Pandit, C. R. J. Org. Chem. 1997, 62, 1543.
32. (b) Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812.
33. (c) Liu, A.; Dillon, K; Campbell, R. M; Cox, D. C.; Huryn, D. M. Tetrahedron Lett. 1996, 37, 3785.
34. (d) Grindley, T. B.; Namazi, H. Tetrahedron Lett. 1996, 37, 991.
35. (e) Valverde, S.; Gómez, A. M.; López, J. C.; Herradón, B. 1996, Tetrahedron Lett. 1996, 37, 1105.