1,2-O-Silyl group rearrangements in carbohydrates - Convenient synthesis of important lactose building blocks

Synlett

Volumn 1995, Issue 9, 1995, Pages 925-927

  Lassaletta, José M ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

1,2 O Silyl migration, reversible; anomeric O alkylation; lactose, 2 O unprotected

Indexed keywords

EID: 79955657835     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5120     Document Type: Article

References (21)

1. This work was supported by the Human Capital and Mobility Program of the EC, the Deutsche Forschungsgemeinschaft, and the Fonds der Chemischen Industrie-J. M. L. is grateful for a stipend in the framework of the Human Capital and Mobility Program.
2. Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212
3. Schmidt, R. R., Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21; and references therein.
4. Sato, S., Nunomura, S., Nakano, T., Ito, Y., Ogawa, T. Tetrahedron Lett. 1988, 29, 4097.
5. Toepfer, A., Schmidt, R. R. Tetrahedron Lett. 1992, 33, 5161
6. Toepfer, A., Kinzy, W., Schmidt, R. R. Liebigs Ann. Chem. 1994, 449.
7. For results with d-G1c, D-Gal, and D-Man derivatives see: Lassaletta, J. M., Meichle, M., Weiler, S., Schmidt, R. R. J. Carbohydr. Chem., submitted for publication. 0-Silyl group migrations in normal diols have been already reported
8. Dodd, G. D., Golding, B. T., Joannon, P. V. J. Chem. Soc. Perkin Trans I 1976, 2273
9. Jones, S. S., Reese, C. B. J. Chem. Soc. Perkin Trans. I 1976, 2762
10. Mulzer, J., Schollhom, B. Angew. Chem. 1990, 102, 433
11. Angew. Chem. Int. Ed. Engl. 1990, 29, 431
12. Watanabe, Y., Fujimoto, T., Ozaki, S. J. Chem. Soc., Chem. Common. 1992, 681
13. Yamazaki, T., Mizutani, K., Kitazume, T. J. Org. Chem. 1993, 58, 4346
14. van Boeckel, C. A. A., van Aelst, S. F., Beetz, T. Reel. Trav. Chim. Pays-Bas 1983, 102, 415
15. Faghih, R., Fraser-Reid, B. Carbohydr. Res. 1987, 169, 247.
16. Reinhardt, S. Universitat Konstanz, unpublished results.
17. Mikamo, M. Carbohydr. Res. 1989, 191, 150.
18. Kinzy, W., Schmidt, R. R. Liebigs Ann. Chem. 1985, 1537.
19. Zemplen, G. Ber. Dtsch. Chem. Ges. 1927, 60, 1555.
20. Klotz, W., Schmidt, R. R. Liebigs Ann. Chem. 1993, 683; J. Carbohydr. Chem. 1994, 13, 1093.
21. The 0-silyl group rearrangement under basic conditions and the ensuing regioselective O-alkylation exhibits some similarity to findings with regioselective alkylations at non-anomeric hydroxy groups in the presence of dibutyltin oxide or bis(tributyl)tin oxide, respectively: Alais, J., Maranduba, A., Veyrieres, A. Tetrahedron Lett. 1983, 24, 2383-2386; Ogawa, T., Matsui, M. Tetrahedron 1981, 37, 2363.