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

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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.

Original languageEnglish
Pages (from-to)835-837
Number of pages3
JournalTetrahedron Letters
Issue number4
Publication statusPublished - 19 Jan 2004


  • Acrocomia mexicana
  • Coyolosa
  • Ether-linked sugars
  • Hypoglycemic

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