Stereocontrolled Synthesis of α-C-Galactosamine Derivatives via Chelation-Controlled C-Glycosylation

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2507-2516

  Urban, Dominique ^a   Skrydstrup, Troels ^a,b   Beau, Jean Marie ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001272931     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971727h     Document Type: Article

References (65)

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16. For several reviews on the synthesis of C-glycosides: (a) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, FL, 1995. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Exeter, U.K., 1995. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677. Postema, M. H. D. Tetrahedron 1992, 48, 8545. (e) Herscovici, J.; Antonakis, K. In Studies in Natural Product Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1992; Vol. 10.
17. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
18. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
19. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
20. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
21. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
22. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
23. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
24. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067. (b) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. Jobron, L.; Leteux, C.; Veyrières, A.; Beau, J.-M. J. Carbohydr. Chem. 1994, 13, 507. (e) Kim, K. H.; Hollingsworth, R. I. Tetrahedron Lett. 1994, 35, 1031. (f) Mbongo, A.; Frèchou, C.; Beaupère, D.; Uzan, R.; Demailly, G. Carbohydr. Res. 1993, 246, 361. (g) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chem. Acta 1996, 79, 1519. (h) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191. (j) Rubinstenn, G.; Esnault, J.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1997, 8, 1327.
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