ChemInform Abstract: Convenient Synthesis of Bicyclic Carbohydrate 1,2-Lactones and Their Stereoselective Opening to 1-Functionalized Glucose Derivatives

Department of Chemistry, University of Potsdam, Karl-Liebknecht-Strasse 24-25, 14476 Potsdam, Germany.
Chemistry - A European Journal (Impact Factor: 5.73). 01/2009; 15(1):49-52. DOI: 10.1002/chem.200802178
Source: PubMed


The convenient synthesis of lactone compounds and their stereoselective transformations by reactions with nucleophiles was reported. The method is applicable for unsaturated hexoses, pentoses, and disaccharide's, and is characterized by high yields and stereoselectivities. The release of carbon dioxide and methanol provides the driving force of the reaction, which favors the lactonization entropically. A convenient and general entry to bicycle carbohydrate 1,2-lactones in only three steps from glycals was developed. The opening of the gluco-configured lactone was demonstrated with various nucleophiles, which enabled the introduction of hetero and carbon substituents at the anomeric position.

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