A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives

Tetrahedron

Volumn 54, Issue 19, 1998, Pages 4839-4848

  Albert, Martin ^a   Karl, Dax ^a   Ortner, Jörg ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXY 2 FLUOROALDOSE DERIVATIVE; CARBOHYDRATE DERIVATIVE; FLUORINE DERIVATIVE; REAGENT; SELECTFLUOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032079602     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00189-6     Document Type: Article

References (36)

1. 1. Glaudemans, C. P. J.; Kovac, P.; Nashed, E. M.; Padlan, E. A.; Arepalli, S. R. Synthetic Oligosaccharides (Ed. Kovac P.), ACS Symp. Ser. 1994, 560, pp. 157-183; Withers, S. G.; Street, I. P.; Percival, M. D. Fluorinated Carbohydrates (Ed. Taylor N. F.), ACS Symp. Ser. 1988, 374, pp. 59-77.
2. 1. Glaudemans, C. P. J.; Kovac, P.; Nashed, E. M.; Padlan, E. A.; Arepalli, S. R. Synthetic Oligosaccharides (Ed. Kovac P.), ACS Symp. Ser. 1994, 560, pp. 157-183; Withers, S. G.; Street, I. P.; Percival, M. D. Fluorinated Carbohydrates (Ed. Taylor N. F.), ACS Symp. Ser. 1988, 374, pp. 59-77.
3. 2. Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 234-277 and ref. cited there.
4. 3. Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 121-181 and ref. cited there.
5. 4. Rozen, S. Chem. Rev. 1996, 96, 1717-1736 and ref. cited there; Adam, M. J.; Pate, B. D.; Nesser, J.-R.; Hall, L. D. Carbohydr. Res. 1983, 124, 215-224; Dax, K., Glänzer, B., Schulz, G., Vyplel, H. Carbohydr. Res. 1987, 762, 13-22.
6. 4. Rozen, S. Chem. Rev. 1996, 96, 1717-1736 and ref. cited there; Adam, M. J.; Pate, B. D.; Nesser, J.-R.; Hall, L. D. Carbohydr. Res. 1983, 124, 215-224; Dax, K., Glänzer, B., Schulz, G., Vyplel, H. Carbohydr. Res. 1987, 762, 13-22.
7. 4. Rozen, S. Chem. Rev. 1996, 96, 1717-1736 and ref. cited there; Adam, M. J.; Pate, B. D.; Nesser, J.-R.; Hall, L. D. Carbohydr. Res. 1983, 124, 215-224; Dax, K., Glänzer, B., Schulz, G., Vyplel, H. Carbohydr. Res. 1987, 762, 13-22.
8. 5. Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755 and ref. cited there.
9. 6. Treatment of simple enol alkyl ethers with 1a or 1b has led to regioselective addition of the respective reagent and/or formation of α-fluoro-carbonyl compounds with total lack of stereoselectivity: Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563-8575.
10. 7. Banks, R. E.; Besheesh, M. K.; Mohialdin-Khaffaf, S. N.; Sharif, I. J. Chem. Soc., Perkin Trans. I, 1996, 2069-2076.
11. 8. For a collection of relevant data see: a) Diksic, M.; Jolly, D. Carbohydr. Res. 1986, 153, 17-24;
12. b) Csuk, R., Glänzer, B. Adv. Carbohydr. Chem. Biochem. 1988, 46, 73-177.
13. 2O: 6 (-203.2 ppm); 7a (-205.7 and 205.9 ppm); 7d (-204.8 and-205.0 ppm);
14. 3OD: 6 (-203.1 ppm); 7b (-206.3 and -207.9 ppm);
15. 2: 6 (-205.1 ppm); 7c (-212.2 ppm);
16. 2O: 6 (-204.3 ppm); 7a (-205.6 and 205.9 ppm); 7e (-208.1 and -208.8 ppm). Characteristic sets of coupling-constants are: 46/25/10 Hz (6); 50/10/3 Hz (α-anomer of 7a, b, d and e); 52/13/4 Hz (β-anomer of 7a, b, d and e) and 50/20/12 Hz (7c); J < 8 Hz in most cases not resolved.
17. 10. The structure of the β-anomer was verified by independent synthesis starting from 8a by means of reduction followed by N-acetylation.
18. 11. Shamma, M.; Deno, N. C.; Remar, J. F. Tetrahedron Lett. 1966, 1375-1379.
19. 12. Czernecki, S.; Vijayakumaran, K.; Ville, G. J. Org. Chem. 1986, 51, 5472-5475.
20. 1-conformer.
21. 1-conformation. O-Acetylation gave 1,3,4-tri-O-acetyl-2-deoxy-2-fluoro-D-arabinopyranose (12d); for data see: M. Bols, I. Lundt, Acta Chem. Scand. 1990, 44, 252-256.
22. 1-conformation. O-Acetylation gave 1,3,4-tri-O-acetyl-2-deoxy-2-fluoro-D-arabinopyranose (12d); for data see: M. Bols, I. Lundt, Acta Chem. Scand. 1990, 44, 252-256.
23. 15. Identified as its peracetate; for data see: Welch, J. T.; Eswarakrishnan, S. J. Chem. Soc., Chem. Commun. 1985, 186-188.
24. 1-conformer of the (2-F-Man)-intermediate; 13.2%.
25. 18. These results will be published elsewhere.
26. 19F NMR data: δ-188.1 ppm (J 45 and 18 Hz) and -207.8 ppm (J 45 Hz); rel. intensities 1:3.
27. 20. a) N-Iodo- and N-bromopyridinium compounds add to glycals under formation of products with 1,2-trans-diaxial arranged substituents (Lemieux, R. U.; Morgan, A. R. Can. J. Chem. 1965, 43, 2205-2213);
28. see also "halogenoglycosyloxylation" (e.g. Thiem, J.; Klaffke, W. J. Org. Chem. 1988, 54, 2006-2009) and "halogenosulphamidation/sulphamidoglycosyloxylation"
29. (Griffith, D. A.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 5811-5819);
30. b) for the reaction with N-fluoropyridinium compounds see ref. 6;
31. c) product 5 from these experiments shows 1,2-trans-diequatorial grouping.
32. 21. For the status of the discussion on the mechanism of electrophilic fluorination see: a) Differding, E; Rüegg, G. M. Tetrahedron Lett. 1991, 31, 3815-3818;
33. b) Differding, E; Wehrli, M. Tetrahedron Lett. 1991, 3819-3822;
34. c) Differding, E.; Bersier, P. M. Tetrahedron 1992, 48, 1595-1604;
35. d) a brief survey on this topic is given in ref. 4, pp. 1749-1752.
36. 22. Syrupy 8b, containing minor impurities, was obtained in 51% yield.