Development of a novel sugar linkage and sugar-related bioactive compounds

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Coyolosa, a new natural product isolated from the Acrocomia mexicana root, has shown a significant effect on fasting blood glucose levels. While there can be no doubt that Coyolosa has a structure with two pyranoses linked at each of their 6-positions, it is less obvious that the stereochemistry of its pyranose moiety corresponds to the proposed structure. In this communication, we report a novel synthesis of 6, 6'-ether-connected pyranoses. Also, we reconsidered the stereochemistry of the proposed structure of Coyolosa based on the structure-activity relationships (SAR) studies. This is the first synthesis of ether-connected sugar based on an acetalization-reduction procedure.