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Synthesis 1987; 1987(2): 174-176
DOI: 10.1055/s-1987-27878
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Regioselektive Acylierung von 1,4:3,6-Dianhydro-D-glucit

Peter Stoss* , Peter Merrath, Günther Schlüter
  • *Chemische Forschung und Entwicklung, Heinrich Mack Nachf., Chem.-Pharm. Fabrik, Postfach 2064, D-7918 Illertissen, West Germany
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Publication Date:
12 September 2002 (online)

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Regioselective Acylation of 1,4:3,6-Dianhydro-D-glucitol Acylation of 1,4:3,6-dianhydro-D-glucitol with anhydrides in the presence of heavy metal salts affords 5-endo-acylates with high regioselectivity, without detectable amounts of the isomeric 2-acylates. Acyl group migration occurs with preference for the 2-exo-position, on heating an acylation mixture, which contains varying amounts of 1,4:3,6-dianhydro-D-glucitol, 2- and 5-monoacylate and 2,5-diacylate, in the presence of reesterification catalysts and whilst distilling off the lower boiling 2-acylate.