The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 372-376

  Huang, Yifang ^a,c   Dalton, David R ^a   Carroll, Patrick J ^b  

^a Temple University   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c SmithKline Beecham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZASUGAR; CARBOHYDRATE DERIVATIVE; POLYOL; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031054288     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962028s     Document Type: Article

References (36)

1. To whom inquiries concerning X-ray crystallography should be addressed.
2. Provencher, L.; Steensma, D. H.; Wong, C.-H. Bioorg. Med. Chem. 1994, 2, 1179.
3. Karpas, A.; Fleet, G. W. J.; Dewk, R. A.; Petrusson, S.; Mangoong, S. K.; Ramsden, J. G.; Jacob, G. S.; Rademacher, T. W. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 9229.
4. (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
5. (b) Sinnott, L. M. Chem. Rev. 1990, 90, 1171.
6. (c) Kajimoto, T.; Liu, K. K.-C.; Pederson, R. L.; Zhong, Z.; Ichikawa, Y.; Porco, J. A.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6187.
7. (d) Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 8293.
8. (e) Liu, K. K.-C.; Kajimoto, T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280.
9. (f) Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett, 1993, 34, 7213.
10. (g) Provencher, L.; Steensma, D. H.; Wong, C.-H. Bioorg. Med. Chem. 1994, 2, 1179.
11. (h) Boutellier, M.; Horenstein, B. A.; Semenyaka, A.; Schramm, B. L.; Ganem, B. Biochemistry 1994, 33, 3994.
12. (i) Deng, H.; Chan, A. W.-Y.; Bagdassarian, C. K.; Dstupiñán, B.; Banem, B.; Callender, R. H.; Schramm, V. L. Biochemistry 1996, 35, 6037.
13. The Amino Sugars; the Chemistry and Biology of Compounds Containing Aminosugars; Jeanloz, R. W., Balazs, D. A., Eds.; Academic Press: New York, 1965-1966; Vols. IA, IB, IIA, IIB.
14. For a preparation of D-iminoribitol [(2R,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see Fleet, G. W. J.; Son, J. C. Tetrahedron 1988, 44, 2647.
15. For a preparation of L-iminoribitol [(2S,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see Fleet, G. W. J.; Son, J. C.; Green, D. St. C.; Cenci di Bello, I.; Winchester, B. Tetrahedron 1988, 44, 2649.
16. For preparation of D-iminoarabinitol [(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685. (b) Ziegler, T.; Straub, A.; Effenberger, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 716. (c) Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asym. 1990, 1, 119. (d) Kajimoto, T.; Chen, L.; Liu, K. K-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
17. For preparation of D-iminoarabinitol [(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685. (b) Ziegler, T.; Straub, A.; Effenberger, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 716. (c) Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asym. 1990, 1, 119. (d) Kajimoto, T.; Chen, L.; Liu, K. K-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
18. For preparation of D-iminoarabinitol [(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685. (b) Ziegler, T.; Straub, A.; Effenberger, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 716. (c) Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asym. 1990, 1, 119. (d) Kajimoto, T.; Chen, L.; Liu, K. K-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
19. For preparation of D-iminoarabinitol [(2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Fleet, G. W. J.; Smith, P. W. Tetrahedron 1986, 42, 5685. (b) Ziegler, T.; Straub, A.; Effenberger, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 716. (c) Fleet, G. W. J.; Witty, D. R. Tetrahedron: Asym. 1990, 1, 119. (d) Kajimoto, T.; Chen, L.; Liu, K. K-C.; Wong, C.-H. J. Am. Chem. Soc. 1991, 113, 6678.
20. For preparation of L-iminoarabinitol [(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Jones, D. W. C.; Nash, R. J.; Bell, E. A.; Williams, J. M. Tetrahedron Lett. 1985, 26, 3125. (b) Reference 3a.
21. For preparation of L-iminoarabinitol [(2S,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Jones, D. W. C.; Nash, R. J.; Bell, E. A.; Williams, J. M. Tetrahedron Lett. 1985, 26, 3125. (b) Reference 3a.
22. For a preparation of D-iminoxylitol [(2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see Ikota, N. Chem. Pharm. Bull. 1989, 37, 3399.
23. For preparation of L-iminoxylitol [(2S,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Buchanan, J. G.; Lumbard, K. W.; Sturgeon, R. J.; Thompson, D. K.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1990, 699. (b) Meng, Q.; Hesse, M. Helv. Chim. Acta 1991, 74, 445.
24. For preparation of L-iminoxylitol [(2S,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) Buchanan, J. G.; Lumbard, K. W.; Sturgeon, R. J.; Thompson, D. K.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1990, 699. (b) Meng, Q.; Hesse, M. Helv. Chim. Acta 1991, 74, 445.
25. For preparation of D-iminolyxitol [(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) reference 3a. (b) Austin, G. N.; Baird. P. D.; Fleet, G. W. J. Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095. (c) Han, S.-Y.; Liddell, P. A.; Joullie, M. M. Synth. Commun. 1988, 18, 275. Reference 6a. (e) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
26. For preparation of D-iminolyxitol [(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) reference 3a. (b) Austin, G. N.; Baird. P. D.; Fleet, G. W. J. Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095. (c) Han, S.-Y.; Liddell, P. A.; Joullie, M. M. Synth. Commun. 1988, 18, 275. Reference 6a. (e) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
27. For preparation of D-iminolyxitol [(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) reference 3a. (b) Austin, G. N.; Baird. P. D.; Fleet, G. W. J. Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095. (c) Han, S.-Y.; Liddell, P. A.; Joullie, M. M. Synth. Commun. 1988, 18, 275. Reference 6a. (e) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
28. For preparation of D-iminolyxitol [(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) reference 3a. (b) Austin, G. N.; Baird. P. D.; Fleet, G. W. J. Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095. (c) Han, S.-Y.; Liddell, P. A.; Joullie, M. M. Synth. Commun. 1988, 18, 275. Reference 6a. (e) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
29. For preparation of D-iminolyxitol [(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see (a) reference 3a. (b) Austin, G. N.; Baird. P. D.; Fleet, G. W. J. Peach, J. M.; Smith, P. W.; Watkin, D. J. Tetrahedron 1987, 43, 3095. (c) Han, S.-Y.; Liddell, P. A.; Joullie, M. M. Synth. Commun. 1988, 18, 275. Reference 6a. (e) Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586.
30. For a preparation of L-iminolyxitol [(2S,3R,4S)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine] see Thompson, D. K.; Hubert, C. N.; Wightman, R. H. Tetrahedron 1993, 49, 3827.
31. Within experimental error, both L- and D-serine yield comparable results. The graphics present the synthetic route showing only the L-isomer for purposes of clarity.
32. Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393.
33. Morikawa, K.; Sharpless, K. B. Tetrahedron Lett. 1993, 34, 5575
34. The X-ray crystal structure of 8 is particularly interesting as there are four molecules in the asymmetric unit. Complete details are provided in the Supporting Information. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
35. This isomer is extraordinarily insoluble in a variety of common and uncommon solvents and its optical rotation was not taken.
36. 13C NMR spectra for intermediates and IR spectra for intermediates and azasugars 1 are provided at: http://astro.ocis.temple.edu/̃dalton/azasugar_1.html.