A Novel Approach to Furanoid Sugars via 1,4-Iodocyclization of Pyranoid D-Galactal

Synlett

Volumn 1996, Issue 12, 1996, Pages 1218-1220

  Jaouen, Véronique ^a   Jégou, Anne ^a   Veyrières, Alain ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002649690     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5709     Document Type: Article

References (30)

1. Mereyala, H. B.; Venkataramanaiah, K. C. J. Chem. Res. (S) 1991, 197; Czernecki, S.; Leteux, C.; Veyrières, A. Tetrahedron Lett. 1992, 33, 221; Leteux, C.; Veyrières, A. J. Chem. Soc., Perkin Trans. 1 1994, 2647.
2. Mereyala, H. B.; Venkataramanaiah, K. C. J. Chem. Res. (S) 1991, 197; Czernecki, S.; Leteux, C.; Veyrières, A. Tetrahedron Lett. 1992, 33, 221; Leteux, C.; Veyrières, A. J. Chem. Soc., Perkin Trans. 1 1994, 2647.
3. Mereyala, H. B.; Venkataramanaiah, K. C. J. Chem. Res. (S) 1991, 197; Czernecki, S.; Leteux, C.; Veyrières, A. Tetrahedron Lett. 1992, 33, 221; Leteux, C.; Veyrières, A. J. Chem. Soc., Perkin Trans. 1 1994, 2647.
4. Lauer, G., Oberdorfer, F. Angew. Chem., Int. Ed. Engl. 1993, 33, 271; Haeckel, R.; Lauer, G.; Oberdorfer, F. Synlett 1996, 21.
5. Lauer, G., Oberdorfer, F. Angew. Chem., Int. Ed. Engl. 1993, 33, 271; Haeckel, R.; Lauer, G.; Oberdorfer, F. Synlett 1996, 21.
6. Kops, J.; Schuerch, C. J. Polym. Sci. Part C 1965, 119; Uryu, T.; Yamanouchi, J.; Kato, T.; Higuchi, S.; Matsuzaki, K. J. Am. Chem. Soc. 1983, 105, 6865.
7. Kops, J.; Schuerch, C. J. Polym. Sci. Part C 1965, 119; Uryu, T.; Yamanouchi, J.; Kato, T.; Higuchi, S.; Matsuzaki, K. J. Am. Chem. Soc. 1983, 105, 6865.
8. Jacquinet, J.-C. Carbohydr. Res. 1990, 199, 153.
9. Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220; Look, G. C.; Ichikawa, Y.; Shen, G.-J.; Cheng, P.-W.; Wong, C.-H. J. Org. Chem. 1993, 58, 4326; Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
10. Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220; Look, G. C.; Ichikawa, Y.; Shen, G.-J.; Cheng, P.-W.; Wong, C.-H. J. Org. Chem. 1993, 58, 4326; Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
11. Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220; Look, G. C.; Ichikawa, Y.; Shen, G.-J.; Cheng, P.-W.; Wong, C.-H. J. Org. Chem. 1993, 58, 4326; Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911.
12. Yamada, S. Tetrahedron Lett. 1992, 33, 2171; Yamada, S. J. Org. Chem. 1992, 57, 1591.
13. Yamada, S. Tetrahedron Lett. 1992, 33, 2171; Yamada, S. J. Org. Chem. 1992, 57, 1591.
14. 5: C, 57.38; H, 7.88. Found: C, 57.25; H, 8.04.
15. 5: C, 37.10; H, 4.81. Found: C, 37.17; H, 4.96.
16. 6: C, 64.66; H, 6.63. Found: C, 64.46; H, 6.89.
17. Deslongchamps, P.; Moreau, C.; Frehel, D.; Atlani, P. Can. J. Chem. 1972, 50, 3402.
18. For X-ray analysis of two 2,7-dioxabicyclo[2.2.1]heptane derivatives see: Dreissig, W.; Luger, P. Acta Cryst. B 1973, 29, 1409; Lynch, V. M.; Mulhern, T. A.; Martin, S. F. Acta Cryst. C 1987, 43, 2237.
19. For X-ray analysis of two 2,7-dioxabicyclo[2.2.1]heptane derivatives see: Dreissig, W.; Luger, P. Acta Cryst. B 1973, 29, 1409; Lynch, V. M.; Mulhern, T. A.; Martin, S. F. Acta Cryst. C 1987, 43, 2237.
20. 7: C, 62.28; H, 7.15. Found: C, 62.64; H, 7.38.
21. Pent-4-enyl glycosides are useful glycosylating reagents: Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927.
22. Mukaiyama, T.; Hirano, N.; Nishida, M.; Uchiro, H. Chem. Lett. 1996, 99.
23. For a study of 2-deoxy-D-galactose see: Overend, W. G.; Shafizadeh, F.; Stacey, M. J. Chem. Soc. 1950, 671.
24. Clark, D. A.; Fuchs, P. L. Synthesis 1977, 628.
25. 2Ph), 4.67 (s, 1H, H-4), 7.06-7.26 (m, 10H, 2xPh).
26. Godoy, J.; Ley, S. V.; Lygo, B. J. Chem. Soc., Chem. Commun. 1984, 1381; Ousset, J. B.; Mioskowski, C.; Yang, Y.-L.; Falck, J. R. Tetrahedron Lett. 1984, 25, 5903.
27. Godoy, J.; Ley, S. V.; Lygo, B. J. Chem. Soc., Chem. Commun. 1984, 1381; Ousset, J. B.; Mioskowski, C.; Yang, Y.-L.; Falck, J. R. Tetrahedron Lett. 1984, 25, 5903.
28. Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223.
29. 2=CH), 7.26-7.38 (m, 10H, 2xPh).
30. For a recent review about glycals in enantiospecific synthesis see Tolstikov, A. G.; Tolstikov, G. A. Russ. Chem. Rev. (Engl. Transl.) 1993, 62, 579.