A synthesis of 2-fluoroglucal derivatives

Tetrahedron Letters

Volumn 47, Issue 45, 2006, Pages 7983-7986

  Boyd, Ewan ^a   Jones, Ray V H ^a   Quayle, Peter ^b  

^a JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^b née Potts), Anita J   (United Kingdom)

Author keywords

Fluorine; Fluorosugar; Glucal; Glycal; Lithiation; Metallation

Indexed keywords

3,4,6 TRI O METHYL DEXTRO GLUCAL; ANION; CARBOHYDRATE; GLUCONATE CALCIUM; PALLADIUM; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; LITHIATION; SYNTHESIS; TEMPERATURE;

EID: 33749250914     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.122     Document Type: Article

References (37)

1. Adam M.J. J. Labelled. Compd. Radiopharm. 42 (1999) 809-813
2. Adam M.J. J. Labelled. Compd. Radiopharm. 45 (2002) 167-180
3. Watts A.G., Opezzo P., Withers S.G., Alzari P.M., and Buschiazzo A. J. Biol. Chem. 281 (2006) 4149-4155
4. Zhou J.-M., Zhou J.-H., Zhang H.-B., Dong X.-C., and Chen M.-B. Carbohydr. Res. 341 (2006) 2224-2232
5. Isanbor C., and O'Hagan D. J. Fluorine Chem. 127 (2006) 303-319
6. Dax K., Albert M., Ortner J., and Paul B.J. Carbohydr. Res. 327 (2000) 47-86
7. Tsuchiya T. Adv. Carbohydr. Chem. Biochem. 48 (1990) 91-277
8. Boeckman R.K., and Bruza K.J. Tetrahedron 37 (1981) 3997-4006
9. Friesen R.W. J. Chem. Soc., Perkin Trans. 1 (2001) 1969-2001
10. Friesen R.W., Sturino C.F., Daljeet A.K., and Kolaczewska A. J. Org. Chem. 56 (1991) 1944-1947
11. Imanieh H., Quayle P., Voaden M., Conway J., and Street S.D.A. Tetrahedron Lett. 33 (1992) 543-546
12. Lesimple P., Beau J.-M., Jaurand G., and Sinaÿ P. Tetrahedron Lett. 27 (1986) 6201-6204
13. Milne J.E., Jarowicki K., Kocienski P.J., and Alonso J. Chem. Commun. (2002) 426-427
14. Milne J.E., and Kocienski P.J. Synthesis (2003) 584-592
15. Whisler M.C., MacNeil S., Snieckus V., and Beak P. Angew. Chem., Int. Ed. 43 (2004) 2206-2225
16. Bridges A.J., Lee A., Maduakor E.C., and Schwartz C.E. Tetrahedron Lett. 33 (1992) 7495-7498
17. Mongin F., and Schlosser M. Tetrahedron Lett. 37 (1996) 6551-6554
18. Snieckus V. Chem. Rev. 90 (1990) 879-933 and references cited therein
19. Burton D.J., and Lu L. Top. Curr. Chem. 193 (1997) 45-90
20. Percy J.M. Top. Curr. Chem. 193 (1997) 131-196
21. Lee J., Tsukazaki M., and Snieckus V. Tetrahedron Lett. 34 (1993) 415-418
22. Funabiki K., Ohtsuki T., Ishihara T., and Yamanaka H. J. Chem. Soc., Perkin Trans. 1 (1998) 2413-2423
23. Bennett A., Percy J.M., and Rok M.H. Synlett (1992) 483-484
24. Boyd, E.; Hallett, M. R.; Jones, R. V. H.; Painter, J. E.; Patel, P.; Quayle, P.; Waring, A. J. Tetrahedron Lett., submitted for publication.
25. Hallett M.R., Painter J.E., Quayle P., Ricketts D., and Patel P. Tetrahedron Lett. 39 (1998) 2851-2852
26. Adamson J., Foster A.B., and Westwood J.H. Carbohydr. Res. 18 (1971) 345-347
27. Korytnyk W., Valentekovic-Horvath S., and Petrie C.R. Tetrahedron 38 (1982) 2547-2550
28. cf. Bessell E.M., Foster A.B., Westwood J.H., Hall L.D., and Johnson R.N. Carbohydr. Res. 19 (1971) 39-48
29. Albert M., Dax K., and Ortner J. Tetrahedron 54 (1998) 4839-4848
30. Lai E.C.K., Morris S.A., Street I.P., and Withers S.G. Bioorg. Med. Chem. 4 (1996) 1929-1937
31. Ciucanu I., and Kerek F. Carbohydr. Res. 131 (1984) 209-217
32. for an alternate preparation of 11 see:. Francisco C.G., Gonzalez C.C., Paz N.R., and Suarez E. Org. Lett. 5 (2003) 4171-4173
33. 5 requires 388.16859; found, 388.1690.
34. Harrity J.P.A., Kerr W.J., and Middlemiss D. Tetrahedron 49 (1993) 5565-5576
35. cf. Painter J.E., Quayle P., and Patel P. Tetrahedron Lett. 36 (1995) 8089-8092
36. Eastham S.A., Herbert J., Painter J.E., Patel P., and Quayle P. Synlett (1998) 61-63
37. For a single previous report of a fluoro-substituted vinyl carbene complex undergoing a Dötz reaction see:. Dötz K.H., and Glaenzer J. J. Chem. Soc., Chem. Commun. (1993) 1036-1037