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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 22
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Original Articles

Improved Synthesis of Methyl 4,6-O-Benzylidene-3-cyano-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside and Methyl 4,6-O-Benzylidene-2,3-dideoxy-3-C-formyl-α-D-erythro-hex-2-enopyranoside

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Pages 3663-3670 | Received 13 Apr 1995, Published online: 23 Sep 2006

References

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  • Inch , T. D. and Lewis , G. J. 1970 . Carbohyd. Res. , 15
  • Sepulchre , A-M. , Luckacs , G. , Vass , G. and Gero , S. D. 1972 . Angew. Chem. Int. Ed. , 11 : 148
  • López , J. C. , Lameignère , E. , Burnouf , C. , Laborde , M. A. , Ghini , A. A. , Olesker , A. and Lukacs , G. 1993 . Tetrahedron , 49 : 7701
  • Davison , B. E. and Guthrie , R. D. 1972 . J. C. S. Perkin I , : 659 and references cited therein
  • Loupy , A. and Tchoubar , B. 1992 . “Salt Effects in Organic and Organometallic Chemistry,” , 22 Weinheim : VCH . 43, 70
  • Hicks , D. R. and Fraser-Reid , B. 1974 . Synthesis , : 203 We slightly modified the procedure described therein. We noticed the formation of the ditosyl derivative, as a by product, was a competitive reaction. In order to minimized it, we found more effective to dissolve the N-tosylimidazole in anhydrous dimethylformamide and slowly add it to the reaction mixture through a dropping funnel with pressure-equalization arm under argon in 45 minutes

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