β-Glycosyl Trifluoroborates as Precursors for Direct α-C-Glycosylation: Synthesis of 2-Deoxy-α-C-glycosides
β-Glycosyl Trifluoroborates as Precursors for Direct α-C-Glycosylation: Synthesis of 2-Deoxy-α-C-glycosides
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β-糖基三氟硼酸盐作为直接 α-C-糖基化的前体：2-脱氧-α-C-糖苷的合成
DOI：
10.1021/acs.orglett.1c00402
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Go Hirai*
中科院分区：
文献类型：
--
作者：
Daiki Takeda;Makoto Yoritate;Hiroki Yasutomi;Suzuka Chiba;Takahiro Moriyama;Atsushi Yokoo;Kazuteru Usui;Go Hirai*
c -糖苷是代谢稳定的天然糖苷模拟物，有望成为研究多糖生物学功能的有用工具。本文描述了在光氧化还原/镍双催化体系下，2-脱氧糖基硼酸衍生物与芳基或乙烯基卤化物通过立体可逆sp3 - sp2交叉偶联反应合成一系列芳基和乙烯基糖苷。乙烯基糖苷的氢化反应得到了c -连接的2 ' -脱氧双糖类似物。
C-Glycosides are metabolically stable mimics of naturalO-glycosides and are expected to be useful tools for investigation of the biological functions of glycans. Here, we describe the synthesis of a series of aryl and vinylC-glycosides by stereoinvertive sp3–sp2cross-coupling reactions of 2-deoxyglycosyl boronic acid derivatives with aryl or vinyl halide, mediated by a photoredox/nickel dual catalytic system. Hydrogenation of the vinylC-glycosides afforded C-linked 2′-deoxydisaccharide analogues.