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

从墨Acrocomia mexicana根中分离得到的新天然产物Coyolosa对空腹血糖水平有显著影响。虽然毫无疑问，Coyolosa的6位上有两个吡喃糖相连的结构，但其吡喃糖部分的立体化学是否与所提出的结构相对应就不那么明显了。在这篇通讯中，我们报道了一种新的6,6 '-醚连接吡喃糖的合成方法。此外，基于构效关系（SAR）的研究，我们重新考虑了拟议结构的立体化学。这是第一个基于缩醛-还原过程的醚连接糖的合成。

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.