Development of a novel sugar linkage and its application to the synthesis of bloactive compounds.

1997年，从Acrocomia mexicana根中分离出coyolosa。值得注意的是，coyolosa是一种通过醚键连接的新碳水化合物，对降低血糖水平具有显着作用。迄今为止，还没有关于糖通过醚键连接的研究报道。因此，我们研究了一种新的醚连接吡喃糖的合成。我们采用了缩醛化-还原法，这是一种在非碱性条件下制备醚类化合物的简便方法。由于两步反应不方便，还研究了一锅还原醚化反应。利用上述方法，合成了各种醚连接的吡喃糖。他们的SAR研究表明，甘露糖连接的吡喃糖具有与coyolosa一样有效的降血糖活性，这表明coyolosa的正确结构将是甘露糖连接的吡喃糖，而不是拟议的阿洛糖连接的结构。我们还研究了利用环氧乙烷的区域选择性开环反应合成醚键连接的稀有糖的新方法，以及利用1C-甲基糖的糖苷化反应合成海藻糖类似物的新方法。

In 1997, coyolosa was isolated from the Acrocomia mexicana root. It is worth noting that coyolosa, which is a new carbohydrate connected by a ether-linkage, shows a significant effect on the decreasing blood glucose level. So far, no studies on the sugar linkage by ether-bonding have ever been reported. Thus, we examined a novel synthesis of ether-connected pyranoses. We adopted an acetalization-reduction procedure, which is a convenient method for the preparation of ethers under non-basic conditions. Since a two-step procedure is inconvenient, the one-pot reductive etherification was also investigated. Utilizing the method mentioned above, various ether-connected pyranoses were synthesized. Their SAR studies showed that the mannose-connected pyranose has the hypoglycemic activity as potent as coyolosa, suggesting that the correct structure of coyolosa would be the mannose-connected pyranose rather than the proposed allose-connected one. We next examined a new approach utilizing regioselective ring opening of oxirane to give the rare sugars connected by ether linkage.A novel synthesis of trehalose analogues by the glycosidation of 1C-methyl sugars is also developed.