Evidence on the structure of coyolosa. Synthesis of 6,6′-ether linked hexoses

Haines, Alan H. (2004) Evidence on the structure of coyolosa. Synthesis of 6,6′-ether linked hexoses. Tetrahedron Letters, 45 (4). pp. 835-837. ISSN 0040-4039

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Abstract

The structure previously reported for coyolosa, a hypoglycemic substance isolated from natural sources, as a 6,6′-ether linked pseudo-disaccharide derived from allose, is incorrect since 6-O-(6-deoxy-D-allos-6-yl)-D-allose 10, synthesised by an unequivocal route, and its derived peracetate 11, both have spectral properties, which differ from those reported for coyolosa and its peracetate. A versatile synthesis has been developed for this type of compound, containing two carbohydrate moieties joined through an ether linkage at their primary centres, which involves the displacement of a primary carbohydrate triflate with a carbohydrate alkoxide, and it allows the preparation of both symmetrical and unsymmetrical representatives of this class of compound.

Item Type: Article
Uncontrolled Keywords: acrocomia mexicana,coyolosa,ether-linked sugars,hypoglycemic,biochemistry,drug discovery,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 14 Jul 2022 12:30
Last Modified: 12 Aug 2022 05:34
URI: https://ueaeprints.uea.ac.uk/id/eprint/86104
DOI: 10.1016/j.tetlet.2003.11.033

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