A one-pot synthesis of glycosyl amides from glycosyl azides using a modified staudinger reaction

Journal of Carbohydrate Chemistry

Volumn 16, Issue 2, 1997, Pages 231-235

  Maunier, Valérie ^a   Boullanger, Paul ^a   Lafont, Dominique ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031527883     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309708006523     Document Type: Article

References (14)

1. D. Lafont, P. Boullanger and Y. Chevalier, J. Carbohydr. Chem., 14, 533 (1995).
2. P. Boullanger, Y. Chevalier, M.-C. Croizier, D. Lafont and M.-R. Sancho, Carbohydr. Res., 278, 91 (1995).
3. P. Boullanger and Y. Chevalier, Langmuir, 12, 1771 (1996).
4. A. Lubineau, J. Auge and B. Drouillat, Carbohydr. Res., 266, 211 (1995).
5. K. Linek, J. Alföldi and M. Durindova, Chem. Pap. - Chem. Zvesti, 47, 247 (1993).
6. D. Plusquellec, C. Brenner-Hénaff, P. Léon-Ruaud, P. Duquenoy, M. Lefeuvre and H. Wroblewski, J. Carbohydr. Chem., 13, 737 (1994).
7. Z. Györgydeak, L. Szilagyi and H. Paulsen, J. Carbohydr. Chem., 12, 139 (1993).
8. Y. G. Gololobov and L. F. Kasukhin, Tetrahedron, 48, 1353 (1992).
9. T. Inazu and K. Kobayashi, Synlett, 869 (1993).
10. The glycosyl phosphinimine intermediate β-5 can anomerize to α-5 via an open-chain zwitterionic structure. (formula presented)
11. E. Zbiral and E. Bauer, Phosphorus, 2, 35 (1972).
12. M. D. Bachi and J. Vaya, J. Org. Chem., 44, 4393 (1979).
13. I. Bosch, A. Gonzalez, F. Urpi and J. Vilarrasa, J. Org. Chem., 61, 5638 (1996).
14. The formation of the C-phosphonium salts 6 cannot be excluded from our experiments. Nevertheless this side-reaction, if any, seems to constitute a very minor pathway.