The C-disaccharide α-C(1→3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human α-1,3-fucosyltransferase VI. Its epimer α-(1→3)-mannopyranoside of N-acetyltalosamine is not

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4251-4260

  Pasquarello, Carla ^a   Picasso, Sylviane ^a   Demange, Raynald ^a   Malissard, Martine ^b   Berger, Eric G ^b   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; FUCOSYLTRANSFERASE; N ACETYLGLUCOSAMINE; PYRANOSIDE;

ARTICLE; CATALYSIS; CELL INTERACTION; DRUG SYNTHESIS; EMBRYO DEVELOPMENT; ENZYME INHIBITION; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ANIMALS; CARBOHYDRATE CONFORMATION; DISACCHARIDES; ENZYME INHIBITORS; FUCOSYLTRANSFERASES; GLYCOSIDE HYDROLASES; HUMANS; INDICATORS AND REAGENTS; KINETICS; MANNOSE; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 0034647558     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991952u     Document Type: Article

References (121)

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20. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
21. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
22. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
23. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
24. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
25. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
26. See, for example, (a) Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. I.; Lowe, J. B.; Ward, P. A. Nature 1993, 364, 149. (b) Hendrix, M.; Wong, C.-H. Pure Appl. Chem. 1996, 68, 2081. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Platt, F. M.; Reinkensmeier, G.; Dwek, R. A.; Butters, T. D. J. Biol. Chem. 1997, 272, 19365. (c) Lapierre, F.; Holme, K.; Lam, L.; Tressler, R. J.; Storm, N.; Wee, J.; Stack, R. J.; Castellot, J.; Tyrrell, D. J. Glycobiology 1996, 6, 355. (d) Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955. Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89. (e) Bols, M. Acc. Chem. Res. 1998, 31, 1. (f) Izumi, M.; Suhara, Y.; Ichikawa, Y. J. Org. Chem. 1998, 63, 4811. Granier, T.; Vasella, A. Helv. Chim. Acta 1998, 81, 865.
27. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
28. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
29. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
30. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
31. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
32. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
33. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
34. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
35. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
36. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
37. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
38. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
39. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
40. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353. Levy, D. E., Tang, C. The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E., Magnus, P. D., Eds.; Pergamon-Elsevier Science Ltd.: Oxford, 1995. Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, FL, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Carbohydrate Mimics, Concept and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1997; Chapter 2, pp 19-48. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502. Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327. Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845. Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561. Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114. Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267. Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697. Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007. Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991. Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31.
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90. For related reactions, see, for example, Koreeda, M.; Jung, K.- Y.;
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