Synthesis of α- and β-carbon-linked serine analogues of the P(k) trisaccharide

Journal of Organic Chemistry

Volumn 64, Issue 25, 1999, Pages 9153-9163

  Debenham, Sheryl D ^a   Cossrow, Jennifer ^a   Toone, Eric J ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIDENE DERIVATIVE; CARBOHYDRATE BINDING PROTEIN; GLYCOSIDE; SERINE DERIVATIVE; TRISACCHARIDE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CONFORMATION; GLYCOSYLATION; HYDROGENATION; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032784298     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991096m     Document Type: Article

References (48)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683-720 and references therein.
2. Wong, C.-H.; Moris-Varas, F.; Hung, S.-C.; Marron, T. G.; Lin, C.-C.; Gong, K. W.; Weitz-Schmidt, G. J. Am. Chem. Soc. 1997, 119, 8152-8158.
3. For other examples see: (a) Simanek, E. E.; McGarvey, G. J.; Jabionowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862. (b) Hummer, G.; Nilsson, U.; Hof, S.; Hindsgaul, O. Abstr. Pap. Am. Chem. Soc. 1998, 215, U112, Part 1.
4. For other examples see: (a) Simanek, E. E.; McGarvey, G. J.; Jabionowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862. (b) Hummer, G.; Nilsson, U.; Hof, S.; Hindsgaul, O. Abstr. Pap. Am. Chem. Soc. 1998, 215, U112, Part 1.
5. For a review of the synthesis and binding studies of multivalent glycoconjugates see: Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692-702.
6. Debenham, S. D.; Toone, E. J. J. Org. Chem., submitted for publication.
7. Vágner, J.; Barany, G.; Lam, K. S.; Krchñák, V.; Sepetov, N. F.; Ostrem, J. A.; Strop, P.; Lebl, M. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8194-8199.
8. O'Brien, A. D.; Tesh, V. L.; Donohue-Rolfe, A.; Jackson, M. P.; Olsnes, S.; Sandvig, K.; Lindberg, A. A.; Keusch, G. T. Curr. Top. Microbiol. Immun. 1992, 180, 65-94.
9. Brown, J. E.; Echeverria, P.; Lindberg, A. A. Rev. Infect. Dis. 1991, 13, S298-S303.
10. Arbus, G. S. Kidney Int. 1997, 58, S91-S96.
11. (a) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094 and references therein.
12. (b) Large, D. G.; Bradshaw, I. J. In Glycopeptides and Related Compounds: Synthesis, Analysis, and Applications; Large, D. G., Warren, C. D., Eds.; Marcel Dekker: New York, Basel, Hong Kong, 1997; pp 311-313.
13. (c) Wakahayashi, K.; Pigman, W. Carbohydr. Res. 1974, 34, 3-14.
14. (d) Manger, I. D.; Rademacher, T. W.; Dwek, R. A. Biochemistry 1992, 31, 10724-10732.
15. (a) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820.
16. (b) Dondoni, A.; Marra, A.; Massi, A. Chem. Commun. 1998, 1741-1742.
17. (c) Urban, D.; Skrydstrup, T.; Beau, J. M. Chem. Commun. 1998, 955-956.
18. (d) Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832.
19. (e) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
20. (f) Arya, P.; Ben, R. N.; Qin, H. P. Tetrahedron Lett. 1998, 39, 6131-6134.
21. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470.
22. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192.
23. (i) Dorgan, B. J.; Jackson, F. W. Synlett 1996, 859-861.
24. (j) Sutherlin, D. P. Stark, T. M.; Hughes, R.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8350-8354.
25. (k) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904.
26. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898.
27. Garegg, P. J.; Hultberg, H. Carbohydr. Res. 1981, 93, C10-C11
28. Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2383-2393.
29. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series Vol. 13; Elsevier Science Inc.: New York, 1995; pp 42-70 and 175-195 and references therein.
30. Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482.
31. Ponten, F.; Magnusson, G. J. Org. Chem. 1996, 61, 7463-7466.
32. Wegmann, B.; Schmidt, R. R. J. Carbohydr. Chem. 1987, 6, 357-375.
33. (a) Woodward, R. B.; Heusler, K.; Gosteli, J.; Naegeli, P.; Oppolzer, W.; Ramage, R.; Ranganathan, S.; Vorbruggen, H. J. Am. Chem. Soc. 1966, 88, 852-4.
34. (b) Carson, J. F. Synthesis 1979, 24-25.
35. Preparation of methyl α-(dimethoxyphosphoryl)-N-tert-butyloxycarbonylglycinate has been previously reported. (a) Zoller, U.; BenIshai, D. Tetrahedron 1975, 31, 863-6. (b) Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
36. Preparation of methyl α-(dimethoxyphosphoryl)-N-tert-butyloxycarbonylglycinate has been previously reported. (a) Zoller, U.; BenIshai, D. Tetrahedron 1975, 31, 863-6. (b) Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
37. Hamada, Y.; Kondo, Y.; Shibata, M.; Shioiri, T. J. Am. Chem. Soc. 1989, 111, 669-673.
38. (a) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125-10138.
39. (b) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423-4424.
40. (c) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375-9376.
41. (d) Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142-5143.
42. 3 and Boc peaks are almost baseline resolved in all cases.
43. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
44. Dasgupta, R.; Anderson, L. Carbohydr. Res. 1994, 264, 155-160.
45. Kuzuhara, H.; Fletcher, H. G. J. Org. Chem. 1967, 32, 2531-2534.
46. (a) Czernecki, S.; Ville, G. J. Org. Chem. 1989, 54, 610-612.
47. (b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
48. DeNinno, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.