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 (former - to 2024)
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	14 Jul 2022 12:30
Last Modified:	25 Sep 2024 16:27
URI:	https://ueaeprints.uea.ac.uk/id/eprint/86104
DOI:	10.1016/j.tetlet.2003.11.033

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