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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 15
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Original Articles

An Efficient Preparation of Silylated Derivatives of L-Erythrulose 3,4-O-Acetals

, , , , &
Pages 2601-2610 | Accepted 12 Dec 1998, Published online: 25 Sep 2007

References

  • Koch , H. and Roper , H. 1988 . Starch Starke , 40 : 121 – 131 .
  • Röper , H. and Koch , H. 1988 . Starch Starke , 40 : 453 – 464 .
  • Carda , M. , Gonzalez , F. , Rodriguez , S. and Marco , J. A . 1992 . Tetrahedron: Asymmetry , 3 : 1511 – 1514 .
  • Carda , M. , Gonzalez , F. , Rodriguez , S. and Marco , J A. 1993 . Tetrahedron: Asymmetry , 4 : 1799 – 1802 .
  • Marco , J. A. , Carda , M. , González , F. , Rodriguez , S. , Murga , J. and Falomir , E. 1995 . An. Quim. , 91 : 103 – 112 .
  • Carda , M. , Falomir , F. , Murga , J. and Marco , J. A . 1996 . J. Chem. Res (S). , : 1
  • Marco , J. A. , Carda , M. , González , F. , Rodriguez , S and Murga , J. 1996 . Liebigs Ann. Chem. , : 1801 – 1810 .
  • Carda , M. , Casabó , P. , González , F. , Rodriguez , S. , Domingo , L. R. and Marco , J. A . 1997 . Tetrahedron: Asymmetry , 8 : 559 – 577 .
  • Marco , J. A. , Carda , M. , Murga , J. , González , F. and Falomir , E. 1997 . Tetrahedron Lett. , : 1841 – 1844 .
  • Marco , J. A. , Carda , M. , González , F. , Rodríguez , S. , Castillo , E. and Murga , M. 1998 . J. Org. Chem. , 63 : 698 – 707 .
  • Carda , M. , Castillo , E. , Rodriguez , S. , Murga , J. and Marco , J. A . 1998 . Tetrahedron: Asymmetry , 9 : 1117 – 1120 .
  • De Wilde , H. , De Clercq , P. , Vandewalle , M. and Roper , H. 1987 . Tetrahedron Lett. , : 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.
  • Dequeker , E. , Compernolle , F. , Toppet , S. and Hoornaert , G. 1995 . Tetrahedron , 51 : 5877 – 5890 .
  • 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.
  • 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.
  • Greene , T. W and Wuts , P. G.M. 1991 . Protective Groups in Organic Synthesis. , 2nd ed. , 60 – 62 . New York : John Wiley and Sons .
  • Marco , J. L . 1988 . J. Chem. Res. (S) , : 276 The TBS derivative of 2a has been previously described:

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