Total asymmetric synthesis of long-chain, branched carbohydrates and of an Aza-C-disaccharide

Tetrahedron Letters

Volumn 37, Issue 12, 1996, Pages 2023-2026

  Frérot, Eric ^a,b   Marquis, Christian ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0040378913     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00189-X     Document Type: Article

References (32)

1. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
2. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
3. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
4. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
5. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
6. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
7. See e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev Biochem. 1988, 57, 785-838; Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653-2658; Feizi, T. In "Carbohydrate Recognition in Cellular Function", Ciba Geigy Symposium 145, Wiley: Chichester, 1989, p. 62-79; Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631-654; Morenem, K. W.; Trimble, R. B.; Hersovics, A. Glycobiology 1994, 4, 113-125; Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303-1306; Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckman, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019-1023.
8. See e.g.: Sinnot, M. L. Chem. Rev. 1990, 90, 1171-1202; Legler, G. Adv. Carbohydr. Chem. Biochem. 1990. 48, 319; Frank, R. W. Bioorganic Chem. 1992, 20, 77-88.
9. See e.g.: Sinnot, M. L. Chem. Rev. 1990, 90, 1171-1202; Legler, G. Adv. Carbohydr. Chem. Biochem. 1990. 48, 319; Frank, R. W. Bioorganic Chem. 1992, 20, 77-88.
10. See e.g.: Sinnot, M. L. Chem. Rev. 1990, 90, 1171-1202; Legler, G. Adv. Carbohydr. Chem. Biochem. 1990. 48, 319; Frank, R. W. Bioorganic Chem. 1992, 20, 77-88.
11. See e.g. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210; Karlsson, G. B.; Butters, T. D.; Dwek, R. A. ; Platt, F. M. J. Biol. Chem. 1993, 268, 570-576.
12. See e.g. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210; Karlsson, G. B.; Butters, T. D.; Dwek, R. A. ; Platt, F. M. J. Biol. Chem. 1993, 268, 570-576.
13. Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 9991-9995.
14. Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, in print.
15. a) Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865-1871;
16. b) Reymond, J.-L.; Vogel, P. Tetrahedron Asymmetry 1990, 1, 729-736;
17. c) Saf, R.; Faber, K.; Penn, G.; Griengl, H.; Tetrahedron 1988, 44, 389-392;
18. d) Ronan, B.; Kagan, H. B. Tetrahedron Asymmetry 1991, 2, 75-90;
19. e) Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979-3982.
20. Vogel, P.; Auberson, Y.; Bimwala, R. M.; de Guchteneere, E.; Vieira, E.; Wagner, J. in "Trends in Synthetic Carbohydrate Chemistry", Eds. Horton, D.; Hawkins, L. D.; McGarvey, G. J. ACS Symposium Series 386; American Chemical Society, Washington, D.C. 1989, p. 197-241; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185.
21. Vogel, P.; Auberson, Y.; Bimwala, R. M.; de Guchteneere, E.; Vieira, E.; Wagner, J. in "Trends in Synthetic Carbohydrate Chemistry", Eds. Horton, D.; Hawkins, L. D.; McGarvey, G. J. ACS Symposium Series 386; American Chemical Society, Washington, D.C. 1989, p. 197-241; Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173-185.
22. Allemann, S.; Vogel, P. Tetrahedron 1994, 50, 2469-2478.
23. 2J = 18.3).
24. Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076-2083.
25. 3J = 7.3, 7.2).
26. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627-2631; Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561-568; Kienzle, F. Helv. Chim. Acta 1975, 58, 1180-1183.
27. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627-2631; Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561-568; Kienzle, F. Helv. Chim. Acta 1975, 58, 1180-1183.
28. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627-2631; Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561-568; Kienzle, F. Helv. Chim. Acta 1975, 58, 1180-1183.
29. 2C(1′)), 0.90(5), 0.13, 0.12 (2s).
30. 3) δ 170.2, 164.6 (2s), 101.4 (d), 97.0, 96.8, 96.2 (3t), 81.6, 80.8, 76.0, 74.6, 70.9, 67.7 (6d), 57.2, 55.7, 55.4 (3q), 56.8 (d), 49.3 (t), 39.7 (d), 26.4 (t), 20.7 (q).
31. For other syntheses of long-chain carbohydrates starting from "naked-sugars", see e.g.: Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843-5854; Chen, Y.; Vogel, P. Ibid, 1994, 59, 2487-2496.
32. For other syntheses of long-chain carbohydrates starting from "naked-sugars", see e.g.: Emery, F.; Vogel, P. J. Org. Chem. 1995, 60, 5843-5854; Chen, Y.; Vogel, P. Ibid, 1994, 59, 2487-2496.