Palladium(0)-Mediated Synthesis of Acetylated Unsaturated 1,4-Disaccharides |
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| Authors: | Isabelle Frappa Boguslaw Kryczka Paul Lhoste Stanislaw Porwanski Denis Sinou Anna Zawisza |
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| Institution: | 1. Laboratoire de Synthèse Asymétrique , associé au CNRS, CPE Lyon, Université Claude Bernard Lyon I , 43, boulevard du 11 Novembre 1918, 69622 , Villeurbanne , Cédex, France E-mail: e-mail: sinou@univ-lyon1.fr;2. Department of Organic and Applied Chemistry , University of Lodz , ul. Naturowicsa 68, 90-136 , Lodz , Poland;3. Laboratoire de Synthèse Asymétrique , associé au CNRS, CPE Lyon, Université Claude Bernard Lyon I , 43, boulevard du 11 Novembre 1918, 69622 , Villeurbanne , Cédex, France E-mail: e-mail: sinou@univ-lyon1.fr;4. Department of Organic and Applied Chemistry , University of Lodz , ul. Naturowicsa 68, 90-136 , Lodz , Poland |
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| Abstract: | Abstract Alkylation of ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (1) with various peracetylated 1-hydroxy sugars in the presence of a catalytic amount of palladium(O) gave the corresponding unsaturated 1,4-disaccharides and trisaccharides. In all cases the reaction is regio- and stereospecific according to the unsaturated moiety, alkylation occuring only at C-4 of the unsaturated carbohydrate, with overall retention of configuration. |
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