Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone |
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| Authors: | Trombotto Stéphane Danel Mathieu Fitremann Juliette Bouchu Alain Queneau Yves |
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| Institution: | Unité Mixte de Sucrochimie CNRS-Béghin-Say (UMR 143), C/o Béghin-Say, C.E.I., 27 boulevard du 11 novembre 1918, B.P. 2132, 69603 Villeurbanne Cedex, France. |
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| Abstract: | The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic or acidic catalysts. |
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