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Synthesis 2000; 2000(4): 525-528
DOI: 10.1055/s-2000-6364
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Selective Synthesis of 4,6-O-Alkenylidene and -Benzylidene Acetals from Unprotected Sucrose by Lanthanide(III) Resin-Catalyzed Transacetalization

S. Porwanski* , P. Salanski, G. Descotes, A. Bouchu, Y. Queneau
  • *Laboratoire de Sucrochimie CNRS - Béghin-Say (UMR 143), c/o Eridania Béghin-Say, 27 Bd du 11 novembre 1918, B.P. 2132, 69603 Villeurbanne Cedex, France; Fax +33 (0) 4 72 44 29 91; E-mail: queneau@univ-lyon1.fr
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Publication Date:
31 December 2000 (online)

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Lanthanide cation exchanged resins were used as catalysts for the acetalization of sucrose. Ytterbium(III)- and erbium(III)-exchanged resins promote the transacetalization of dialkyl acetals of α,β-unsaturated aldehydes. A two-step one-pot procedure provides direct access from the unsaturated aldehyde to a series of sucrose 4,6-acetals in good yields from unprotected sucrose without concomitant glycosidic bond cleavage.

sucrose - acetals - lanthanides - heterogeneous catalysis - carbohydrates - resins - transacetalization

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