Synthesis of α-c(1 ← 3)-mannopyranoside of N-acetylgalactosamine, a new β-galactosidase inhibitor

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 5, 1999, Pages 793-796

  Pasquarello, Carla ^a   Demange, Raynald ^a   Vogel, Pierre ^a  

^a BCH 3307   (Switzerland)

Author keywords

C glycosidation; Carbohydrate mimetics; Enzyme inhibitors

Indexed keywords

BETA GALACTOSIDASE; ENZYME INHIBITOR; N ACETYLGALACTOSAMINE; PYRANOSIDE;

ACETYLATION; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; ENZYMATIC ASSAY; ENZYME INHIBITOR INTERACTION; GLYCOSYLATION; REACTION ANALYSIS; SYNTHESIS;

ACETYLGALACTOSAMINE; ANIMALS; ASPERGILLUS; BETA-GALACTOSIDASE; CHICKENS; ENZYME INHIBITORS; FABACEAE; LIVER; MANNOSE; PLANTS, MEDICINAL; RHIZOPUS;

PHASEOLUS (ANGIOSPERM);

EID: 0033535437     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00064-5     Document Type: Article

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25. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
26. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
27. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
28. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
29. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
30. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
31. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
32. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
33. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
34. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
35. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
36. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354; Levy, D. E., Tang, C. The Chemistry of C-Glycosides, Tetrahedron Organic Chemistry Series, Eds.: Baldwin, J. E.; Magnus, P. D. 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, Ed: Chapleur, Y.; Wiley-VCH, Weinheim, 1997, Chap. 2, p. 19-48; Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959; Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1897; Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. 1996, 2, 502-510; Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215-2218; Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336; Angelaud, R.; Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1997, 38, 8845-8848; Bornaghi, L.; Utille, J.-P.; Rekai, E. D.; Mallet, J.-M.; Sinaÿ, P.; Driguez, H. Carbohydr. Res. 1997, 305, 561-568; Dondoni, A.; Zuurmond, H. M.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124; Sutherlin, D. P.; Armstrong, R. W. Ibid. 1997, 62, 5267-5283; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Lett. 1998, 39, 3697-3700; Du, Y.; Polat, T.; Linhardt, R. J. Ibid. 1998, 39, 5007-5010; Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Ibid. 1998, 39, 7991-7994; Zhu, Y.-H.; Vogel, P. Ibid. 1998, 39, 31-34.
37. See e.g.: MacLean, G. D.; Bowen-Yacyshyn, M. B., Samuel, J.; Meikle, A.; Stuart, G.; Nation, J.; Poppema, S.; Jerry, M.; Koganty, R., Wong, T.; Longenecker, B. M. J. Immunother. 1992, 11, 292-305; Rye, P. D.; Bovin, N. V.; Vlasova, E. V.; Walker, R. A. Glycobiology 1995, 5, 385-389.
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43. Sinaÿ, P. Pure & Appl. Chem. 1997, 69, 459-463.
44. Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327-1336.
45. Giese, B.; Witzel, T. Angew. Chem. Int. Ed. Engl. 1986, 25, 450-451.
46. Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076-2083.
47. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077-2092.
48. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 1, 173-185; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979-3982.
49. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 1, 173-185; Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979-3982.
50. Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. 1995, 60, 8351-8359.
51. Ferritto, R.; Vogel, P. Synlett 1996, 281-282.
52. -1.
53. 3J=9.2, 6.7, H-7').
54. 3) δ: 172.1, 170.5, 170.4, 170.0, 169.7 (5s), 132.6 (s, C-3), 129.4 (d, C-4), 72.0, 70.8, 69.9, 69.8, 69.6, 68.3, 68.0 (7d), 62.8 (t, C-1'), 48.2 (d, C-5), 33.0 (d, C-6), 26.5 (t, C-7'), 23.2, 21.0, 20.9, 20.8, 20.6 (5q).
55. Krimen, L. I.; Cota, D. J. Org. React. 1969, 17, 213-325.
56. Gasparini, F., Vogel, P. J. Org. Chem. 1990, 55, 2451-2457; Pitzer, K.; Hudlicky, T. Synlett 1995, 803-805; Yan, F.; Nguyen, B. V.; York, C.; Hudlicky, T. Tetrahedron 1997, 53, 11541-11548.
57. Gasparini, F., Vogel, P. J. Org. Chem. 1990, 55, 2451-2457; Pitzer, K.; Hudlicky, T. Synlett 1995, 803-805; Yan, F.; Nguyen, B. V.; York, C.; Hudlicky, T. Tetrahedron 1997, 53, 11541-11548.
58. Gasparini, F., Vogel, P. J. Org. Chem. 1990, 55, 2451-2457; Pitzer, K.; Hudlicky, T. Synlett 1995, 803-805; Yan, F.; Nguyen, B. V.; York, C.; Hudlicky, T. Tetrahedron 1997, 53, 11541-11548.
59. 3).
60. •+), 616 (36), 71 (100).
61. Appropriate p-nitrophenyl glycoside substrates buffered to optimum pH of the enzymes were used; for details, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, B.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812.