Stereospecific synthesis of chiral caprolactone monomers from D-glucose.

Defossemont, Guylaine and Mincher, David (2003) Stereospecific synthesis of chiral caprolactone monomers from D-glucose. Carbohydrate Research, 338 (6). pp. 563-565. ISSN 0008-6215

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The synthesis and characterisation of a novel chiral bicyclic oxacaprolactone is reported. The choice of diisopropylidene- -glucose as a starting material allowed selective introduction of the synthetic equivalent necessary for the formation of the seven-membered ring of the lactone, i.e., one carbon atom and the carbonyl of the ester which was to become the carbonyl group of the lactone. In order to complete the formation of the seven-membered ring, via intramolecular lactonisation, it was necessary to excise carbon six and to establish a primary alcohol group at C-5. The lactone was fully characterised and available for ring-opening polymerisation.

Item Type: Article
Print ISSN: 0008-6215
Uncontrolled Keywords: Caprolactone; Diisopropylidene- -glucose; NMR; Stereospecific synthesis
University Divisions/Research Centres: Faculty of Health, Life & Social Sciences > School of Life Sciences
Dewey Decimal Subjects: 500 Science > 540 Chemistry > 547 Organic chemistry
Library of Congress Subjects: Q Science > QD Chemistry
Item ID: 1679
Depositing User: RAE Import
Date Deposited: 04 Jul 2008 08:20
Last Modified: 13 Jun 2013 13:43

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