通过H-膦酸酯衍生物的O-选择性糖基化立体选择性合成α-糖基亚磷酸酯和亚磷酰胺。
Stereoselective synthesis of alpha-glycosyl phosphites and phosphoramidites via O-selective glycosylation of H-phosphonate derivatives.
作者信息
Matsumura Fumiko, Oka Natsuhisa, Wada Takeshi
机构信息
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, Kashiwa, Chiba, Japan.
出版信息
Org Lett. 2008 Nov 20;10(22):5297-300. doi: 10.1021/ol802190x. Epub 2008 Oct 28.
A highly stereo- and chemoselective glycosylation of H-phosphonate derivatives with glycosyl iodides was discovered as a reverse reaction of the formation of a glycosyl iodide from a glycosyl phosphite and I- under mild acidic conditions. Further study on the unique reaction showed that the reaction provided various alpha-glycosyl phosphites and phosphoramidites in a highly stereoselective manner with complete O-selectivity.
发现H-膦酸酯衍生物与糖基碘化物的高度立体和化学选择性糖基化反应是在温和酸性条件下由亚磷酸糖酯和碘离子形成糖基碘化物的逆反应。对该独特反应的进一步研究表明，该反应以高度立体选择性的方式提供了各种α-糖基亚磷酸酯和亚磷酰胺，具有完全的O-选择性。
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