Ichikawa Yoshiyasu, Matsukawa Yohei, Tamura Mari, Ohara Fumiyo, Isobe Minoru, Kotsuki Hiyoshizo
Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan.
Chem Asian J. 2006 Nov 20;1(5):717-23. doi: 10.1002/asia.200600190.
A new method for the synthesis of urea-linked disaccharides in aqueous media has been developed. The key feature of our approach is two strained Steyermark-type gluco- and galactopyranosyl oxazolidinones. Each oxazolidinone is attached to a pyranose ring in a di-equatorial trans-annulation framework. Reaction of these oxazolidinones with 4-aminohexopyranose in water proceeded smoothly to afford the urea-tethered cellobiose and lactose analogues. The galactose-type oxazolidinone proved to be more reactive than the glucose-type, which is explained by the presence of an axial hydroxy group at C4 in the former.
已开发出一种在水性介质中合成尿素连接二糖的新方法。我们方法的关键特征是两个具有张力的施泰尔马克型葡萄糖和吡喃半乳糖恶唑烷酮。每个恶唑烷酮在双赤道跨环框架中连接到一个吡喃糖环上。这些恶唑烷酮与4-氨基己吡喃糖在水中顺利反应，得到尿素连接的纤维二糖和乳糖类似物。结果表明，半乳糖型恶唑烷酮比葡萄糖型更具反应性，这是由于前者在C4位存在一个轴向羟基。
