The synthesis of C-trisaccharides exploiting the stereochemical diversity of a central sugar

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9802-9803

  Sutherlin, Daniel P ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TRISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0029860709     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960741t     Document Type: Article

References (40)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130.
2. (b) Feizi, T. Curr. Opin. Struct. Bio. 1993, 3, 701.
3. (c) Varki, A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7390.
4. (a) Paulson, J. C. The Receptors; Academic: New York, 1985; Vol. 2.
5. (b) Wharton, S. A.; Weis, W.; Skehel, J. J.; Wiley, D. C. The Influenza Virus; Plenum: New York, 1989.
6. (a) Gyler, M.; Rose, D.; Bundle, D. Science 1991, 253, 442.
7. (b) Boren, T.; Falk, P.; Roth, K. A.; Larson, G.; Normark, S. Science 1993, 262, 1892.
8. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Ferez, M.; Sinhal, A. K.; Halcomori, S.; Paulson, J. C. Science 1990, 250, 1130.
9. (b) Higashi, H.; Hirabayashi, Y.; Fukui, Y.; Naiki, M.; Matsumoto, M.; Ueda, S.; Kato, S. Cancer Res. 1985, 45, 3796-3802.
10. (a) Butcher, E. C. Am. J. Path. 1990, 1, 3-11.
11. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M. J.; Phillips, M. L.; Wagner, E.; Nudelman, E.; Sinhal, A. K.; Hakomori, S.; Paulson, J. C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224.
12. (a) Bertozzi, C. R. Chem. Biol. 1995, 11, 703-708.
13. (b) Mulligan, M. S.; Paulson, J. C.; De Frees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149-151.
14. Postema, M. H. D. Tetrahedron 1992, 48, 8545.
15. (a) Haneda, T.; Goekjian, P.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490-498.
16. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160.
17. (c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432-9436.
18. Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743.
19. Sutherlin, D. P.; Hughes R.; Stark, T. M.; Armstrong, R. W. Manuscript in review.
20. Armstrong, R. W.; Sutherlin, D. P.; Wolinski, L. Presented at the 31st Annual ACS Western Regional Meeting, San Diego, CA, October 18-21, 1995.
21. This process is parallel to Janda's recursive deconvolution of combinatorial libraries. Erb, E.; Janda, K. D.; Brenner, S. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11422.
22. Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383.
23. Derived in four steps from N-acetylglucosamine and described fully in the supporting information.
24. (a) Dyer, U. C.; Kishi, Y. J. Org. Chem. 1988, 53, 3383-3384.
25. (b) Kishi Y. Pure Appl. Chem. 1992, 64, 343-350.
26. The stereochemistry of the protected allylic alcohol 13 was elucidated by X-ray crystallography.
27. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
28. Dess, D. B.; Martin, J. C. J Org. Chem. 1983, 48, 4156-4157.
29. Ireland, R. E.; Liu, L. J Org. Chem. 1993, 58, 2899-2900.
30. 3 would provide the opposite regiochemistry and should permit entry into these diastereomers. See ref 16.
31. Brown, H. C.; Jadhau, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535-1538. This assignment was further confirmed by NMR analysis of the tetrabenzylated 11.
32. Compounds 8 and 9 could be separated via chromatography following an acetylation step.
33. These sugars may alternatively be referred to as 2,4-dideoxy-L-glucose for 8 and 2,4-dideoxy-D-idose for 9 due to the lack of the hydroxyl on C-4 found in the natural hexoses.
34. Two fractions were obtained, one with 10% contamination by the other diastereomer and the other with a 15% contamination of the previous diastereomer.
35. Or 2,4-dideoxy-L-gulose for 10 and 2,4-dideoxy-D-talose for 11.
36. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
37. Wang, Y.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 468-481.
38. H-1′ (for the center sugar) in the precursor to 6 is coupled to H-2′ with a large J value of 9.8 Hz, indicative of a trans-trans diaxial relationship. H-3′ is coupled to H-2′ (10.4 Hz), H-4′ axial (10.4 Hz), and to H-4′ equatorial (4.2 Hz). H-4′ equatorial, in addition to H-3′ coupling and a geminal coupling to H-4′ axial (12.0 Hz), is weakly coupled to H-5′, a pattern similar to the H-4 proton of galactose found in a previously synthesized C-1, C- 2 branched C-trisaccharide (see ref 8a).
39. Or 2,4-dideoxy-D-glucose for 6 and 2,4-dideoxy-L-idose for 7.
40. Sufficient quantities for biological assays were obtained for all compounds.