Diastereoselective synthesis of 1-deoxytalonojirimycin

Synlett

Volumn , Issue 2, 1999, Pages 204-206

  Ruiz, María ^a   Ojea, Vicente ^a   Quintela, José María ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

1,4 diol oxidation; Chiral glycine equivalent; Imino sugar; Syn aldol; lactol

Indexed keywords

1 DEOXYTALONOJIRIMYCIN; GLYCINE; IMINO ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENZYME ACTIVITY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; VIRUS INFECTION;

EID: 0032939466     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3155     Document Type: Article

References (36)

1. Although in broad usage, the term aza sugar is incorrect. It should be restricted to structures where carbon, not oxygen, is replaced by a nitrogen. For IUPAC recommendations on the nomenclature of carbohydrates, see: Pure & Appl. Chem. 1996, 68, 1919-2008.
2. a. Ganem, B. Acc. Chem. Res. 1996, 29, 340-347.
3. b. Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190.
4. Elbein, A. D.; Kaushal, G. P. Methods Enzymol. 1994, 230, 316-329.
5. a. Gross, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935-944.
6. b. Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605-611.
7. c. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210.
8. Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 135-162.
9. Raadt, A.; Ekhart, C. W.; Ebner, M.; Stütz, A. E. Top. Curr. Chem. 1997, 187, 157-186.
10. Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313-314.
11. a. Liu, K. K.-C.; Kajimoto, T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280-6289.
12. b. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173-179.
13. Hashimoto, H; Hayakawa, M. Chem. Lett. 1989, 1881-1884.
14. a Reunión Bienal de la Real Sociedad Española de Química. Cádiz, September 1997 (ISBN 84-7786-458-6. vol 2, pp. 1057-1058).
15. b. Ojea, V.; Ruiz, M; Quintela, J. M. Synlett 1997, 83-84.
16. c. Ruiz, M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1996, 37, 5743-5746.
17. For other synthesis of amino sugars based on aldol reactions of chiral glycine anions, see: Mukaiyama, T. in Trends in Synthetic Carbohydrate Chemistry, Horton, D., Hawkins, L. D., McGarvey, G. J. Eds. ACS Symposium Series 386, page 280, 1989.
18. Cohen, N.; Banner, B. L.; Laurenzano, A. J.; Carozza, L. Org. Synth., Coll. Vol. VII 1990, 297-301.
19. 2,3-O-Isopropylidene-D-erythrose is a useful chiral synthon in diastereoselective synthesis, see: a. Gypser, A.; Peterek, M.; Scharf, H.-D. J. Chem. Soc., Perkin Trans. 1, 1997, 1013-1016.
20. b. Pearsons W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217-7221.
21. c. Gypser, A.; Flasche, M.; Scharf, H.-D. Liebigs Ann. Chem. 1994, 775-778.
22. d. Thompson, D. K.; Hubert, C. N.; Wightman, R. H. Tetrahedron 1993, 49, 3827-3840, and references cited in reference 12.
23. a. Mekki, B.; Singh, G.; Wightman, R. H. Tetrahedron Lett. 1991, 32, 5143-5146.
24. b. Bukowick, R. R.; Wilcox, C. S. J. Org. Chem. 1988, 53, 463-471.
25. c. Buchanan J. G.; Jigajinni, V. B.; Singh, G.; Wightman, R. H. J. Chem. Soc. Perkin Trans. 1 1987, 2377-2383, and references cited therein.
26. d. Corey, E. J.; Pan, B.-C.; Duy, H. H.; Deardoff, D. R. J. Am. Chem. Soc. 1982, 104, 6816-6818.
27. Williams, R. Synthesis of Optically Active α-Amino Acids. Baldwin, J. E.; Magnus, P. D. Eds. Pergamon Press: Oxford 1989.
28. Grauert, M.; Schöllkopf, U. Liebigs Ann. Chem. 1985, 1817-1824, and references cited therein.
29. Both enantiomers of 2,5-dimethoxy-3-isopropyl-3,6-dihydropyrazine can be purchased from Merck. 2,3-O-Isopropylidene-L-erythrose is accessible, in a one-pot procedure, from the inexpensive L-(+)-arabinose. See: a. Kiso, M.; Hasegawa, A. Carbohydr. Res. 1976, 52, 95. See also reference 13d.
30. 1H NMR spectrum of the mixture of adducts.
31. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908-919.
32. 2).
33. Corey, E. J.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488.
34. O-Iodoxybenzoic acid (IBX) was prepared as described in: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022.
35. See for example: 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, 8569-8572.
36. 13C NMR and FABMS spectral data obtained for this material were also in accordance with the literature values (see references 7, 8 or 9).