An efficient preparation of silylated derivatives of L-erythrulose 3,4- O-acetals

Synthetic Communications

Volumn 29, Issue 15, 1999, Pages 2601-2610

  Carda, M ^a   Rodriguez S ^a   Murga, J ^a   Falomir, E ^a   Marco, J A ^b   Roper H ^c  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c Eridania Beghin Say   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

KETOTETROSE LEVO ERYTHRULOSE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; REPRODUCIBILITY; SYNTHESIS;

EID: 0032993311     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908086420     Document Type: Article

References (17)

1. (a) Koch, H. and Röper, H. Starch/Stärke 1988, 40, 121-131.
2. (b) Röper, H.; Koch, H. Starch/Stärke 1988, 40, 453-464.
3. (a) Carda, M., González, F., Rodriguez, S., and Marco, J.A. Tetrahedron: Asymmetry 1992, 3, 1511-1514
4. (b) Carda, M., González, F., Rodríguez, S., and Marco, J A., Tetrahedron: Asymmetry 1993, 4, 1799-1802.
5. (c) Marco, J.A., Carda, M., González, F., Rodríguez, S., Murga, J., and Falomir, E An.Quim. 1995, 91, 103-112.
6. (d) Carda, M., Falomir, F., Murga, J., and Marco, J.A. J.Chem.Res (S). 1996, 1.
7. (e) Marco, J.A., Carda, M., González, F., Rodríguez, S., and Murga, J., Liebigs Ann.Chem. 1996, 1801-1810.
8. (f) Carda, M., Casabó, P., González, F., Rodríguez, S., Domingo, L.R., and Marco, J.A., Tetrahedron: Asymmetry 1997, 8, 559-577.
9. (g) Marco J.A., Carda, M., Murga, J., González, F., and Falomir, E., Tetrahedron Lett. 1997, 1841-1844.
10. (h) Marco, J.A., Carda, M., González, F., Rodríguez, S., Castillo, E., and Murga, M. J.Org.Chem. 1998, 63, 698-707.
11. (i) Carda, M., Castillo, E., Rodriguez, S., Murga, J., and Marco, J.A. Tetrahedron: Asymmetry 1998, 9, 1117-1120.
12. De Wilde, H., De Clercq, P., Vandewalle, M., and Röper, H. Tetrahedron Lett. 1987, 4757-4758. Later modifications of the original method were privately communicated to us by Dr. J. Van der Eycken, from the University of Ghent, Belgium. However, even these modified procedures did not give satisfactory results in our hands, either.
13. Dequeker, E., Compernolle, F., Toppet, S., and Hoornaert, G. Tetrahedron 1995, 51, 5877-5890.
14. A minimum amount of MeOH in the solvent (see Experimental) was necessary in the first azeotropic drying for a sufficient solubilization of the erythrulose hydrate. In the second evaporation, however, toluene alone was used. We have found that the presence of methanol or products which release methanol in the reaction conditions (e.g. 2,2-dimethoxypropane or similar acetals) was undesirable, as it leads to the formation of further by-products with concomitant yield decrease.
15. An increase of the reaction time above the indicated value (12 h) with the aim of increasing the degree of conversion only resulted in a yield decrease and the formation of more by-products.
16. Greene, T.W. and Wuts, P.G.M. Protective Groups in Organic Synthesis. 2nd ed., John Wiley and Sons, New York, 1991, pp. 60-62.
17. The TBS derivative of 2a has been previously described: Marco, J.L. J.Chem.Res. (S) 1988, 276.