Synthesis of a 5-hydroxypiperidine-2,3,4,6-tetramethanol, a new 2,6- dideoxy-2,6-iminoheptitol derivative

Journal of Organic Chemistry

Volumn 64, Issue 24, 1999, Pages 8973-8975

  Jotterand, Nathalie ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; NOTE; ORGANIC CHEMISTRY;

EID: 0033607758     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991228b     Document Type: Note

References (38)

1. See, for example, (a) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (b) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297 and refs cited therein.
2. See, for example, (a) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (b) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297 and refs cited therein.
3. Ekhart, C. W.; Fechter, M. H.; Hadwiger, P.; Mlaker, E.; Stütz, A. E.; Tauss, A.; Wrodnigg, T. M. In Iminosugars as Glycosidase Inhibitors, Nojirimycin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; pp 254-390.
4. See, for example, (a) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Nojirimycin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; pp 216-251 and references therein. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605.
5. See, for example, (a) Elbein, A. D.; Molyneux, R. J. In Iminosugars as Glycosidase Inhibitors; Nojirimycin and Beyond; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; pp 216-251 and references therein. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605.
6. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
7. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
8. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
9. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
10. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
11. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
12. See, for example, (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215. (b) Dennis, J. W.; Koch, K.; Beckner, D. J. Nat. Cancer Inst. 1989, 81, 1028. (c) Pal, R.; Hoke, G. M.; Sarngadharan, M. G. Proc. Natl. Acad. Sci. U.S.A. 1989, 89, 3384. (d) Johnson, V. A.; Walker, B. D.; Barlow, M. A.; Paradis, T. J.; Chou, T. C.; Hirsch, M. S. Antimicrob. Agents Chemother. 1989, 33, 53. (e) Goss, P. E.; Baptiste, J.; Fernandes, B.; Baker, M.; Dennis, J. W. Cancer Res. 1994, 54, 1450. (f) Mehta, A.; Lu, X.; Block, T. M.; Blumberg, B. S.; Dwek, R. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 1822. (g) Fenouillet, E.; Papandreou, M. J.; Jones, I. M. Virology 1997, 231, 89.
13. (a) Kite, G. C.; Fellows, L. E.; Fleet, G. W. J.; Liu, P. S.; Scofield, A. M. Smith, N. G. Tetrahedron Lett. 1988, 29, 6483.
14. (b) Fleet, G. W. J.; Namgoong, S. K.; Barker, C.; Baines, S.; Jacob, G. S.; Winchester, B. Tetrahedron Lett. 1989, 30, 4439.
15. (c) Winchester, B.; Barker, C.; Baines, S.; Jacob, G. S.; Namgoong, S. K.; Fleet, G. W. J. Biochem. J. 1990, 265, 275.
16. (d) Bruce, I.; Fleet, G. W. J.; Cenci di Bello, I.; Winchester, B. Tetrahedron 1992, 48, 10191.
17. (e) Holt, K. E.; Leeper, F. J.; Handa, S. J. Chem. Soc., Perkin Trans. 1 1994, 231.
18. (f) Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R., Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
19. (g) Shilvock, J. P.; Wheatley, J. R.; Davis, B.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; Müller, M.; Crook, S.; Watkin, D. J.; Smith, C.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8569.
20. (h) Parr, I. B.; Horenstein, B. A. J. Org. Chem. 1997, 62, 7489.
21. Baudat, A.; Picasso, S.; Vogel, P. Carbohydr. Res. 1996, 281, 277.
22. 10
23. Whiters, S. G.; Namchuk, M.; Mosi, R. In Iminosugars as Glycosidase Inhibitors; Nojirimycin and Beyond, Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; pp 188-206.
24. Schaller, C.; Demange, R.; Picasso, S.; Vogel, P. Bioorg. Med. Chem. Lett. 1999, 9, 277.
25. Pasquarello, C.; Demange, R.; Vogel, P. Bioorg. Med. Chem. Lett. 1999, 9, 793.
26. Brown, G. M. Dubreuil, P. Can. J. Chem. 1963, 46, 1577.
27. Jotterand, N.; Vogel, P. Synlett 1998, 1237.
28. Jotterand, N.; Vogel, P.; Schenk, K. Helv. Chim. Acta 1999, 82, 821.
29. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
30. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
31. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
32. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
33. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
34. (a) For related processes, see, for example, (a) Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1984, 25, 4029. (b) Beaupère, D., Stasik, B.; Uzan, R.; Demailly, G. Carbohydr. Res. 1989, 191, 163. (c) Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926. (d) Behling, J.; Farid, P.; Medich, J. R.; Scaros, M. G.; Prunier, M.; Weier, R. M.; Khanna, I. Synth. Commun. 1991, 27, 1383. (e) de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189. (f) Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487.
35. Theurillat-Moritz, V.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 3163.
36. p-Nitrophenyl β-galactopyranogide was used as substrate buffered to optimum pH of the enzymes; for details see (a) Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1. (b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, B.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806.
37. p-Nitrophenyl β-galactopyranogide was used as substrate buffered to optimum pH of the enzymes; for details see (a) Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1994, 1, 1. (b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, B.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806.
38. Kraehenbuehl, K.; Picasso, S.; Vogel, P. Helv. Chim. Acta 1998, 81, 1439.