Oroszova Beata, Choutka Jan, Pohl Radek, Parkan Kamil
Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague 6 (Czech Republic).
Chemistry. 2015 May 4;21(19):7043-7. doi: 10.1002/chem.201406591. Epub 2015 Mar 20.
This work reports a modular and rapid approach to the stereoselective synthesis of a variety of α- and β-(1→2)-linked C-disaccharides. The key step is a Ni-catalyzed cross-coupling reaction of D-glucal pinacol boronate with alkyl halide glycoside easily prepared from commercially available D-glucal. The products of this sp(2) -sp(3) cross-coupling reaction can be converted to glucopyranosyl, mannopyranosyl, or 2-deoxy-glucopyranosyl C-mannopyranosides by one- or two-step stereoselective oxidative-reductive transformations. To the best of our knowledge, we demonstrated the first synthetic application of a challenging sp(2) -sp(3) Suzuki-Miyaura cross-coupling reaction in carbohydrate chemistry.
这项工作报道了一种模块化且快速的方法，用于立体选择性合成多种α-和β-(1→2)连接的C-二糖。关键步骤是镍催化的D-葡糖醛酸频哪醇硼酸酯与由市售D-葡糖醛酸轻松制备的烷基卤代糖苷的交叉偶联反应。这种sp(2)-sp(3)交叉偶联反应的产物可通过一步或两步立体选择性氧化还原转化，转化为吡喃葡萄糖基、甘露吡喃糖基或2-脱氧吡喃葡萄糖基C-甘露吡喃糖苷。据我们所知，我们展示了具有挑战性的sp(2)-sp(3)铃木-宫浦交叉偶联反应在碳水化合物化学中的首次合成应用。
