PharmaQAM, Department of Chemistry, Université du Québec à Montréal, PO Box 8888, Succ. Centre-Ville, Montréal (Québec), Canada H3C 3P8.
Carbohydr Res. 2011 Sep 6;346(12):1479-89. doi: 10.1016/j.carres.2011.03.041. Epub 2011 Apr 6.
A small library of bivalent α-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl α-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling.
为了评估糖间距离对与植物和细菌凝集素的多价结合相互作用的影响，构建了一个具有刚性连接子的二价α-D-甘露吡喃糖苷的小文库。为此，合成了碘芳基和炔丙基α-D-甘露吡喃糖苷，并在前一种情况下用钯化学处理 TMS-乙炔以提供相应的乙炔基芳基衍生物。然后使用路易斯酸催化的糖苷化、芳基-芳基同偶联、过渡金属催化的 Sonogashira 交叉偶联反应和氧化 Glaser 同偶联反应，获得了 15 个二聚体成员的文库。
