Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Gottingen, Tammannstr. 2, D-37077 Göttingen, Germany.
Org Lett. 2010 Sep 3;12(17):3934-7. doi: 10.1021/ol101625p.
A flexible and robust method for the assembly of (1-->6)-linked C-glycosidic disaccharides is presented. The key reaction is a Pd-catalyzed coupling of 1-iodo- or 1-triflato-glycals with alkynyl glycosides. Reinstallation of the native hydroxyl group pattern is achieved after selective hydrogenation of the triple bond using Raney-nickel. Epoxidation with DMDO and reductive epoxide opening gives access to either the alpha- or the beta-derivative, depending on the hydride source.
本文提出了一种灵活、稳健的（1-->6）-连接 C-糖苷二糖的组装方法。关键反应是 Pd 催化的 1-碘代或 1-三氟甲磺酸基糖与炔基糖苷的偶联。使用雷尼镍选择性还原三键后，重新安装了天然的羟基模式。用 DMDO 环氧化和还原环氧化物开环，可以根据氢化物源得到α-或β-衍生物。
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