Regioselective <em>O</em>-Glycosylation of Nucleosides <em>via</em> the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Hidehisa Someya; Taiki Itoh; Mebae Kato; Shin Aoki

doi:10.3791/57897

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Chemistry

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苷 2 ', 3 ' -二醇酯对双糖苷合成的选择性O-糖基化

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2′,3′-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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苷 2 ', 3 ' -二醇酯对双糖苷合成的选择性O-糖基化

DOI:

10.3791/57897-v

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08:46 min

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July 26, 2018

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Hidehisa Someya, Taiki Itoh, Mebae Kato, Shin Aoki²

¹Faculty of Pharmaceutical Sciences,Tokyo University of Science, ²Imaging Frontier Center,Tokyo University of Science

Chapters

00:04Title
00:51Procedure for O-Glycosylation Reactions
05:59NMR Studies of Cyclic Boronic Ester
07:28Results: O-Glycosylations of Nucleosides Utilizing Temporary Protection of 2 ,3 -Diol by Boronic Ester
08:08Conclusion

Summary

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在这里, 我们提出了合成双糖苷的协议, 选择性O-糖基化的 ribonucleosides通过临时保护其 2 ', 3 '-二醇的基团利用循环硼酸酯。该方法适用于几种不受保护的苷, 如腺苷、鸟嘌呤、胞苷、苷、5-methyluridine 和 5-fluorouridine, 给予相应的双糖苷。

苷 2 ', 3 ' -二醇酯对双糖苷合成的选择性O-糖基化

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