Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition

Journal of the American Chemical Society

Volumn 118, Issue 29, 1996, Pages 6826-6840

  Lin, Chun Cheng ^a   Shimazaki, Makoto ^a   Heck, Marie Pierre ^a   Aoki, Shin ^a   Wang, Ruo ^a   Kimura, Teiji ^a,b   Ritzèn, Helena ^a   Takayama, Shuichi ^a   Wu, Shih Hsiung ^a,c   Weitz Schmidt, Gabriel ^a,d   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b EISAI CO LTD   (Japan)

^c INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^d Preclinical Research   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; PHOSPHITE; SIALIC ACID DERIVATIVE;

ARTICLE; ENZYME SYNTHESIS; GLYCOSYLATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; STEREOCHEMISTRY;

EID: 0011238336     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952265x     Document Type: Article

References (108)

1. Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123.
2. Kondo, H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 8748.
3. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Dibenzyl diethylphosphoramidate (DDP) is commercially available from Aldrich Chemical Co., Inc.
4. (a) Müller, T.; Hummel, G.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 325.
5. (b) Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16.
6. (c) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1993, 34, 1765.
7. (d) Sugai, T.; Ritzèn, H.; Wong, C.-H. Tetrahedron: Asymmetry 1993, 4, 1051.
8. (e) Sim, M. M.; Kondo, H.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 2260.
9. (f) Corey, E. J.; Lee, J. J. Am. Chem. Soc. 1993, 115, 8871.
10. (a) Hashimoto, S.; Umeo, K.; Sano, A.; Watanabe, N.; Nakajima, N.; Ikegami, S. Tetrahedron. Lett. 1995, 36, 2251.
11. (b) Watanabe, Y.; Nakamoto, C.; Ozaki, S. Synlett 1993, 115.
12. For a review involved in the effects of protecting groups and stereochemistry on the reactivity of glycosylation reagents on O-glycosylations. see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Paulsen, H. Chem. Soc. Rev. 1984, 13, 15. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823. (d) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (e) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
13. For a review involved in the effects of protecting groups and stereochemistry on the reactivity of glycosylation reagents on O-glycosylations. see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Paulsen, H. Chem. Soc. Rev. 1984, 13, 15. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823. (d) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (e) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
14. For a review involved in the effects of protecting groups and stereochemistry on the reactivity of glycosylation reagents on O-glycosylations. see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Paulsen, H. Chem. Soc. Rev. 1984, 13, 15. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823. (d) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (e) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
15. For a review involved in the effects of protecting groups and stereochemistry on the reactivity of glycosylation reagents on O-glycosylations. see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Paulsen, H. Chem. Soc. Rev. 1984, 13, 15. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823. (d) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (e) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
16. For a review involved in the effects of protecting groups and stereochemistry on the reactivity of glycosylation reagents on O-glycosylations. see: (a) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. (b) Paulsen, H. Chem. Soc. Rev. 1984, 13, 15. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823. (d) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. (e) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
17. For a review involved in the synthesis of C-glycosides, see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press, Inc.: Boca Raton, FL, 1995; pp 1-377. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Jaramillo, C.; Knapp, S. Synthesis 1994, 1.
18. For a review involved in the synthesis of C-glycosides, see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press, Inc.: Boca Raton, FL, 1995; pp 1-377. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Jaramillo, C.; Knapp, S. Synthesis 1994, 1.
19. For a review involved in the synthesis of C-glycosides, see: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press, Inc.: Boca Raton, FL, 1995; pp 1-377. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (c) Jaramillo, C.; Knapp, S. Synthesis 1994, 1.
20. y: Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701.
21. y: Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701.
22. (a) Hakomori, S. Adv. Cancer Res. 1989, 52, 257.
23. (b) Varki, A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7390.
24. (c) Lasky, L. A. Science 1992, 258, 964.
25. (d) Springer, T. A.; Lasky, L. A. Nature 1991, 349, 196.
26. (e) Feizi, T. TIBS 1991, 16, 84.
27. Tril, P. A.; Willner, D.; Lasch, S. J.; Henderson, A. J.; Hofstead, S.; Casazza, A. M.; Firestone, R. A.; Hellström, I.; Hellström, K. E. Science 1993, 261, 212.
28. Fell, H. P.; Yarnold, S.; Hellström, I.; Hellström, K. E.; Folger, K. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 8507.
29. Hellström, I.; Garrigues, H. J.; Garrigues, U.; Hellström, K. E. Cancer Res. 1990, 50, 2183.
30. Jeffrey, P. D.; Bajorath, J.; Chang, C.-Y. Y.; Yelton, D.; Hellström, I.; Hellström, K. E.; Sheriff, S. Nature Struct. Biol. 1995, 2, 466.
31. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1132.
32. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Bevilacqua, M.; Seed, B. Science 1990, 250, 1130.
33. (c) Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, R. M. Cell 1990, 63, 475.
34. (d) Kameyama, A.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res. 1991, 209, C1.
35. (e) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C.-H. J. Chem. Soc., Chem. Commun. 1991, 870.
36. (f) Danishefsky, S. J.; Gervay, J.; Perterson, J. M.; McDonald, F. E.; Koseki, K.; Oriyama, T.; Griffith, D. A. J. Am. Chem. Soc. 1992, 114, 8329.
37. (g) Singh, K.; Fernández-Mayoralas, A.; Lomas, M. J. J. Chem. Soc., Chem. Commun. 1994, 775.
38. (h) Palcic, M. M.; Venot, A.; Ratcliffe, R. M.; Hindsgaul, O. Carbohydr. Res. 1989, 190, 1.
39. For the free conformation, see: (a) Ichikawa, Y.; Lin, Y.-C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (b) Ball, G. E.; O'Neill, R. A.; Schultz, J. E.; Lowe, J. B.; Weston, B. W.; Nagy, J. O.; Brown, E. G.; Hobbs, C. J.; Bendnarski, M. D. J. Am. Chem. Soc. 1992, 114, 5449.
40. For the free conformation, see: (a) Ichikawa, Y.; Lin, Y.-C.; Dumas, D. P.; Shen, G.-J.; Garcia-Junceda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283. (b) Ball, G. E.; O'Neill, R. A.; Schultz, J. E.; Lowe, J. B.; Weston, B. W.; Nagy, J. O.; Brown, E. G.; Hobbs, C. J.; Bendnarski, M. D. J. Am. Chem. Soc. 1992, 114, 5449.
41. For the bound conformation based on transfer NOE, see: (c) Cooke, R. M.; Hale, R. S.; Lister, S. G.; Shah, G.; Weir, M. P. Biochemistry 1994, 33, 10591. (d) Scheffler, K.; Ernst, B.; Katopodis, A.; Magnani,J. L.; Wang, W. T.; Weisemann, R.; Peters, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1841.
42. For the bound conformation based on transfer NOE, see: (c) Cooke, R. M.; Hale, R. S.; Lister, S. G.; Shah, G.; Weir, M. P. Biochemistry 1994, 33, 10591. (d) Scheffler, K.; Ernst, B.; Katopodis, A.; Magnani,J. L.; Wang, W. T.; Weisemann, R.; Peters, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 1841.
43. Graves, B. J.; Crowther, R. L.; Chandran, C.; Rumberger, J. M.; Li, S.; Huang, K. S.; Presky, D. H.; Familletti, P. C.; Wolitzky, B. A.; Burns, D. K. Nature 1994, 367, 532.
44. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
45. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
46. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
47. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
48. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
49. - group of the NeuAc residue are essential: (a) Stahl, W.; Sprengard, U.; Kretzschmar, G.; Kunz, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 2096. (b) Ramphal, J. Y.; Zheng, Z.-L.; Perez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459. (e) DeFrees, S. A.; Gaeta, F. C. A.; Lin, Y.-C.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1993, 115, 7549. (d) Brandley, B. K.; Kiso, M.; Abbas, S.; Nikrad, P.; Srivastava, O.; Foxall, C.; Oda, Y.; Hasegawa, A. Glycobiology 1993, 3, 633. (e) Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B. K. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 10372. (f) Nelson, R. M.; Dolish, S.; Aruffo, A.; Cecconi, O.; Bevilacqua, M. P. J. Clin. Invest. 1993, 91, 1157.
50. (a) Bamford, M. J.; Bird, M.; Gore, P. M.; Holmes, D. S.; Priest, R.; Prodger, J. C.; Saez, V. Bioorg. Med. Chem. Lett. 1996, 6, 239.
51. (b)-Thoma, G.; Schwarzenbach, F.; Duthaler, R. O. J. Org. Chem. 1996, 61, 514.
52. (c) Huang, H.; Wong, C-H. J. Org. Chem. 1995, 60, 3100.
53. (d) Uchiyama, T.; Vassilev, V. P.; Kajimoto, T.; Wong, W.; Huang, H; Lin, C.-C.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 5395.
54. (e) Kogan, T. P.; Dupye, B.; Keller, K. M.; Scott, I. L.; Bui, H.; Market, B. V.; Beck, P. J.; Voytus, J. A.; Revelle, B. M.; Scott, D. J. Med. Chem. 1995, 38, 4976.
55. (f) Bertozzi, C. R. Chem. Biol. 1995, 2, 703.
56. (g) DeFrees, S. A.; Kosch, W.; Way, W.; Paulson, J. C.; Sabesan, S.; Halcomb, R. L.; Huang, D.-H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1995, 117, 66.
57. (h) Prodger, J. C.; Bamford, M. J.; Gore, P. M.; Holms, D. S.; Saez, V.; Ward, P. Tetrahedron Lett. 1995, 36, 2339.
58. (i) Hanessian, S.; Prabhanjan, H. Synlett 1994, 868.
59. (j) Allanson, N. M.; Davidson, A. D.; Martin, F. M. Tetrahedron Lett. 1993, 34, 3945.
60. (k) Ragan, J. A.; Cooper, K. Bioorg, Med. Chem. Lett. 1994, 4, 2563.
61. Narasinga Rao, B. N.; Anderson, M. B.; Musser, J. H.; Gilbert, J. H.; Schaefer, M. E.; Foxall, C.; Brardley, B. K. J. Biol. Chem. 1994, 269, 19663.
62. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
63. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
64. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
65. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
66. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
67. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
68. For other syntheses of C-aryl glycosides, see: (a) Mahling, J.-A.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 461. (b) Ramaiah, P. A.; Row, L. R.; Reddy, D. S.; Anjaneyulu, A. S. R.; Ward, R. S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1 1979, 2313. (c) Eade, R. A.; Pham, H.-P. Aust. J. Chem. 1979, 32, 2483. (d) Mahling, J.-A.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 467. (e) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289. (f) Schmidt, R. R.; Hoffmann, M. Tetrahedron Leu. 1982, 23, 409. (g) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1989, 30, 833.
69. Ueno, T.; Kurihara, N.; Hashimoto, S.; Nakajima, M. Agric. Biol. Chem. 1967, 31, 1346.
70. Lemieux, R.; Bundle, D. R.; Baker, D. A. J. Am. Chem. Soc. 1975, 97, 4076.
71. Garegg, P. J.; Hultberg, H.; Oscarson, S J. J. Carbohydr. Chem. 1983, 2, 305.
72. Takayama, S.; Shimazaki, M.; Wong, C.-H. Bioorg. Med. Chem. Lett., in press.
73. (a) Nicolaou, K. C.; Caufield, T. J.; Kataoka, H.; Stylianides, N. A. Carbohydr. Res. 1990, 202, 177.
74. (b) Lacombe, J. M.; Pavia, J. Org. Chem. 1983, 48, 2557.
75. (c) Garg, H. G.; Jeanloz, R. W. Carbohydr. Res. 1976, 49, 482.
76. Polt, R.; Szabò, L.; Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249.
77. Compounds 28, 31, and 33 were purchased from Bachem Bioscience Inc., and 29, 30, 32, and 34-36 were prepared from the corresponding amino acids according to a reported procedure; see: Wang, S.-S.; Gisin, B. F.; Winter, D. P.; Makotske, R.; Kulesha, I. D. J. Org. Chem. 1977, 42, 1287.
78. For the synthesis of 37, see: Takada, H.; Takagi, S.; Kawakubo, H. Bull. Chem. Soc: Jpn. 1994, 67, 1196.
79. For the synthesis of 38, see: Faber, K.; Hönig, H.; Seufer-Wasserthal, P. Tetrahedron Lett. 1988, 29, 1903.
80. For the synthesis of 65, see: Wu, S.-H.; Shimazaki, M.; Lin, C.-C.; Qiao, L.; Moree, W. J.; Weitz-Schmidt, G.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1996, 35, 88.
81. For the synthesis of 59, see: Vassilev, V. P.; Uchiyama, T.; Kajimoto, T.; Wong, C.-H. Tetrahedron Lett. 1995, 36, 4081.
82. For the synthesis of 60, see: Nakamura, Y.; Shin, C. Chem. Lett. 1992, 49.
83. For the synthesis of 62, see: Fitz, W.; Schwark, J.-R.; Wong, C.-H. J. Org. Chem. 1995, 60, 3663.
84. (a) Dong, Z.; Butcher Jr., J. A. Tetrahedron Lett. 1991, 32, 5291.
85. (b) Greilich, U.; Zimmermann, P.; Jung, K. H.; Schmidt, R. R. Liebigs Ann. Chem. 1993, 859.
86. x polymer instead of HL-60 cells was used: Weitz-Schmidt, G.; Stokmaier, D.; Scheel, G.; Nifant'ev, N. E.; Tuzikov, A. B.; Bovin, N. V. Ann. Biochem., in press.
87. Feather, M. S.; Harris, J. F. J. Org. Chem. 1965, 30, 153 and references cited therein.
88. For a recent investigation of the hydrolysis of n-pentenyl glycosides, see: Wilson, B. G.; Fraser-Reid, B. J. Org. Chem. 1995, 60, 317.
89. (a) Lemieux, R. U. Chem. Soc. Rev. 1978, 7, 423.
90. (b) Mukaiyama, T.; Murai, Y.; Shoda, S. I.; Chem. Lett. 1981, 431.
91. (c) Ogawa, T.; Yamamoto, H.; Nukada, T.; Kitajima, T.; Sugimoto, M. Pure Appl. Chem. 1984, 56, 779.
92. (d) Fugedi, P.; Garegg, P. J.; Lonn, H.; Norberg, T. Glycoconjugate J. 1987,4, 97.
93. (e) Mootoo, D. R.; Konradsson, P.; Udodong, U. Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583.
94. (f) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
95. (g) Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881.
96. (h) Suzuki, K.; Maeta, H. Matsumoto, T. Tetrahedron Lett. 1989, 36, 4853.
97. (i) Sinay, P. Pure Appl. Chem. 1991, 63, 519.
98. (j) Nicolau, K. C.; Caulfield, T. J.; Groneberg, R. D. Pure Appl. Chem. 1991, 63, 555.
99. (k) Garegg, P. J. Ace. Chem. Res. 1992, 25, 575.
100. (l) Kanie, O.; Hindsgaul, O. Curr. Opin. Struct. Biol. 1992, 2, 674.
101. (m) Boons, G.-J. Tetrahedron 1996, 52, 1095.
102. For comparison of various glycosylation methods, see: (a) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 5, pp 283-330. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14. 1043. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1432.
103. For comparison of various glycosylation methods, see: (a) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 5, pp 283-330. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14. 1043. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1432.
104. For comparison of various glycosylation methods, see: (a) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods; Ernst, B., Leumann, C., Eds.; Verlag Helvetica Chimica Acta: Basel, Switzerland, 1995; Vol. 5, pp 283-330. (b) Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14. 1043. (c) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1432.
105. (a) Paulsen, H.; Kolar, C.; Stenzel, W. Chem. Ber. 1978, 11, 2370.
106. (b) Flowers, H. M.; Jeanloz, R. W. J. Org. Chem. 1963, 28, 1377.
107. (a) Rueger, H.; Benn, M. H. Can, J. Chem. 1982, 60, 2918.
108. (b) VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23 1973.