A flexible route to mannose 6-phosphonate functionalized derivatives

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 177, Issue 10, 2002, Pages 2363-2377

  Vidal, Sébastien ^a   Montero, Jean Louis ^a   Leydet, Alain ^a   Morère, Alain ^a  

^a UNIV MONTPELLIER   (France)

Author keywords

Glycolipid; Lectin; Mannose 6 phosphate; Mannose 6 phosphate insulin like growth factor; Mannose 6 phosphonate triethyleneglycolcholesteryl; Phosphonation; Tris(trimethylsilyl)phosphite

Indexed keywords

CARBOHYDRATE DERIVATIVE; MANNOSE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; THIN LAYER CHROMATOGRAPHY;

EID: 0036811183     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500214297     Document Type: Article

References (49)

1. S. Kornfeld, Annu. Rev. Biochem., 61, 307 (1992).
2. M. Stein, J. E. Zijderhand-Bleekemolen, H. Geuze, A. Hasilik, and K. von Figura, EMBO J., 6, 2677 (1987).
3. J. X. Kang, Y. Li, and A. Leaf, Proc. Natl. Acad. Sci. USA, 95, 13671 (1998).
4. B. Schmidt, C. Kiecke-Siemsen, A. Waheed, T. Braulke, and K. von Figura, J. Biol. Chem., 270, 14975 (1995).
5. P. G. Marron-Terrada, M. A. Brzycki-Wessel, and N. M. Dahms, J. Biol. Chem., 273, 22358 (1998).
6. J. X. Kang, J. Bell, A. Leaf, R. L. Beard, and R. A. S. Chandraratna, Proc. Natl. Acad. Sci. USA, 95, 13687 (1998).
7. C. Vidil, A. Morère, M. Garcia, V. Barragan, B. Hamdaoui, H. Rochefort, and J.-L. Montero, Eur. J. Org. Chem., 447 (1999).
8. C. Vidil, S. Vidal, A. Morère, and J.-L. Montero, Phosphorus, Sulfur, and Silicon, 158, 125 (2000).
9. R. Rabinowitz, J. Org. Chem., 28, 2975 (1963).
10. P. Le Marechal, C. Froussios, M. Level, and R. Azerad, Carbohydr. Res., 94, 1 (1981).
11. C. Garbay-Jaureguiberry, D. Ficheux, and B. P. Roques, Int. J. Peptide Protein Res., 39, 523 (1992).
12. M. F. Wang, M. M. L. Crilley, B. T. Golding, T. McInally, D. H. Robinson, and A. Tinker, J. Chem. Soc., Chem. Commun., 667 (1991).
13. V. Barragan, F. M. Menger, K. L. Caran, C. Vidil, A. Morère, and J.-L. Montero, Chem. Commun., 85 (2001).
14. A. F. Rosenthal and L. A. Vargas, Tetrahedron Lett., 977 (1975).
15. K. Jones and W. W. Mood, Carbohydr. Res., 155, 217 (1986).
16. H. H. Baer, L. R. Breton, and Y. Shen, Carbohydr. Res., 200, 377 (1990).
17. H. H. Baer, Y. Shen, and X. Wu, Carbohydr. Res., 241, 117 (1993).
18. A. De Raadt, H. Griengl, and N. Klempier, J. Org. Chem., 58, 3179 (1993).
19. G. O. Aspinall, A. G. McDonald, and R. K. Sood, Can. J. Chem., 72, 247 (1994).
20. D. El Garrouj, S. Aliau, A. Aumelas, and J.-L. Borgna, J. Med. Chem., 38, 2339 (1995).
21. Z. Pakulski and A. Zamojski, Polish J. Chem., 68, 1109 (1994).
22. H. H. Baer and H. R. Hanna, Carbohydr. Res., 102, 169 (1982).
23. Z. Pakulski and A. Zamojski, Tetrahedron, 51, 871 (1995).
24. D. Rouzaud and P. Sinaÿ, J. Chem. Soc., Chem. Commun., 1353 (1983).
25. P. G. Goekjian, T.-C. Wu, H.-Y. Kang, and Y. Kishi, J. Org. Chem., 56, 6422 (1991).
26. C. Barbaud, M. Bols, and I. Lundt, Tetrahedron, 51, 9063 (1995).
27. M. A. Leeuwenburgh, S. Picasso, H. S. Overkleeft, G. A. van der Marel, P. Vogel, and J. H. van Boom, Eur. J. Org. Chem., 1185 (1999).
28. Y.-C. Xin, Y.-M. Zhang, J.-M. Mallet, C. P. J. Glaudemans, and P. Sinaÿ, Eur. J. Org. Chem., 471 (1999).
29. R. Anderson, Synthesis, 717 (1985).
30. C. Burford, F. Cooke, G. Roy, and P. Magnus, Tetrahedron, 39, 867 (1983).
31. P. A. M. van der Klein and J. H. van Boom, Carbohydr. Res., 224, 193 (1992).
32. Q. Shen, D. G. Sloss, and D. B. Berkowitz, Synth. Commun., 24, 1519 (1994).
33. D. B. Berkowitz, M. Bose, T. J. Pfannenstiel, and T. Doukov, J. Org. Chem., 65, 4498 (2000).
34. T.-L. Ho, H. C. Ho, and C. M. Wong, J. Chem. Soc., Chem. Commun., 791 (1972).
35. T.-H. Chuang, J.-M. Fang, W.-T. Jiaang, and Y.-M. Tsai, J. Org. Chem., 61, 1794 (1996).
36. I. E. Marko, A. Ates, A. Gautier, B. Leroy, J.-M. Plancher, Y. Quesnel, and J.-C. Vanherck, Angew. Chem. Int. Ed., 38, 3207 (1999).
37. B. Bernet and A. Vasella, Helv. Chim. Acta, 62, 1990 (1979).
38. B. Bernet and A. Vasella, Helv. Chim. Acta, 62, 2400 (1979).
39. J. Hooz and S. S. H. Gilani, Can. J. Chem., 46, 86 (1968).
40. D. Seebach and E. J. Corey, J. Org. Chem., 40, 231 (1975).
41. S. Hanessian, Preparative Carbohydrate Chemistry, S., Hanessian, ed. (Marcel Dekker, New York, 1997), p 263.
42. P. Collins and R. Ferrier, Monosaccharides: Their Chemistry and Their Roles in Natural Products (Wiley & Sons: New York, 1995).
43. D. Lafont, P. Boullanger, and S. Chierici, New J. Chem., 20, 1093 (1996).
44. W. Wang and F. Kong, J. Org. Chem., 63, 5744 (1998).
45. W. Wang and F. Kong, Tetrahedron Lett., 39, 1937 (1998).
46. D. Crich, Z. Dai, and S. Gastaldi, J. Org. Chem., 64, 5224 (1999).
47. W. Wang and F. Kong, Tetrahedron Lett., 40, 1361 (1999).
48. W. Wang and F. Kong, J. Org. Chem., 64, 5091 (1999).
49. W. Wang and F. Kong, Angew. Chem., Int. Ed. Engl., 38, 1247 (1999).