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Synthesis 1998; 1998(2): 157-161
DOI: 10.1055/s-1998-2009
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Coniferin and Derivatives: a Fast and Easy Synthesis via the Aldehyde Series Using Phase-Transfer Catalysis

Nicolas Daubresse* , Charlette Francesch, Farida Mhamdi, Christian Rolando
  • *Ecole Normale Supérieure, Département de Chimie, URA 1679 du CNRS, Processus d'Activation Móleculaire, 24 rue Lhomond, 75231 Paris Cedex 05, France; Fax + 33(1)44 32 34 65; E-mail: chr@roxane.ens.fr
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Publikationsdatum:
31. Dezember 2000 (online)

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Coniferin was synthesised in good yields (56% starting from vanillin) under mild conditions. A one-pot coupling of the glucosidation and Wittig-type reactions led to coniferaldehyde tetra-O-acetylglucoside, easily reduced into tetra-O-acetylconiferin by sodium borohydride. Similar procedures were used for the synthesis of syringin and the glucoside of 4-coumaryl alcohol.

coniferin - lignin - phase transfer - syringin - Wittig