Silyl group migration in 1-O-silyl protected sugars-convenient synthesis of 2-O-unprotected sugars

Journal of Carbohydrate Chemistry

Volumn 15, Issue 2, 1996, Pages 241-254

  Lassaletta, José M ^a   Meichle, Michaela ^a   Weiler, Sven ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030546376     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005442     Document Type: Article

References (19)

1. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
2. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
3. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
4. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
5. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
6. G. H. Dodd, B. T. Golding, and P. V. Ioannon, J. Chem. Soc. Perkin Trans I, 2273 (1976); S. S. Jones and C. B. Reese, J. Chem. Soc., Perkin Trans I, 2762 (1979); J. Mulzer and B. Schöllhorn, Angew. Chem. (1990); Angew. Chem. Int. Ed. Engl. 29, 431 (1990); Y. Watanabe, T. Fujimoto, and S. Ozaki, J. Chem. Soc., Chem. Commun., 681 (1992); T. Yamazaki, K. Mizutani, and T. Kitazume, J. Org. Chem. 58, 4346 (1993).
7. C. A. A. van Boeckel, S. F. van Aelst, and T. Beetz, Recl. Trav. Chim. Pays-Bas 102, 415 (1983); R. Faghih and B. Fraser-Reid, Carbohydr. Res. 169, 247 (1987).
8. C. A. A. van Boeckel, S. F. van Aelst, and T. Beetz, Recl. Trav. Chim. Pays-Bas 102, 415 (1983); R. Faghih and B. Fraser-Reid, Carbohydr. Res. 169, 247 (1987).
9. G. Ekborg, B. Lindberg, and J. Lonngren, Acta Chem. Scand. 26, 3287 (1972); R. R. Schmidt and G. Effenberger, Carbohydr. Res. 171, 59 (1987).
10. G. Ekborg, B. Lindberg, and J. Lonngren, Acta Chem. Scand. 26, 3287 (1972); R. R. Schmidt and G. Effenberger, Carbohydr. Res. 171, 59 (1987).
11. S. Hanessian, D. M. Dixit, and T. J. Liak, Pure Appl. Chem. 53, 129 (1981); M. G. Hoffmann, Dissertation, Univ. Konstanz, 1985.
12. S. Hanessian, D. M. Dixit, and T. J. Liak, Pure Appl. Chem. 53, 129 (1981); M. G. Hoffmann, Dissertation, Univ. Konstanz, 1985.
13. R. R. Schmidt and M. Stumpp, Liebigs Ann. Chem., 1249 (1983); and references therein.
14. G. Zemplén, Ber. Dtsch. Chem. Ges. 60, 1555 (1927).
15. O-Deacetylation of 1-O-TDS-and 1-O-TBMS-protected sugars under Zemplén conditions at room temperature resulted generally in silyl migrations and higher migratory aptitude was found for the TBDMS group: M. Meichle, R. Windmüller, and R. R. Schmidt, unpublished results.
16. E. G. Gros and V. Deulofeu, J. Org. Chem. 29, 3647 (1964); P. Zimmermann and R. R. Schmidt, Liebigs Ann. Chem., 663 (1988).
17. E. G. Gros and V. Deulofeu, J. Org. Chem. 29, 3647 (1964); P. Zimmermann and R. R. Schmidt, Liebigs Ann. Chem., 663 (1988).
18. J. J. Patroni, R. V. Stick, B. W. Skelton, and A. H. White, Aust. J. Chem. 41,91 (1988).
19. Cis-1,3-0-silyl group migrations in 1,3-diols have been already observed: Y. Torisawa, N. Shibasaki, and S. Ikegami, Chem. Pharm. Bull. 31, 2607 (1983).