Indirect synthetic route to α-L-fucosides via highly stereoselective construction of α-L-galactosides followed by C6-deoxygenation
Indirect synthetic route to α-L-fucosides via highly stereoselective construction of α-L-galactosides followed by C6-deoxygenation
复制标题
通过高度立体选择性构建 α-L-半乳糖苷，然后进行 C6-脱氧，间接合成 α-L-岩藻糖苷
DOI：
10.1039/d0ob01128b
复制
发表时间：
2020
影响因子：
3.2
通讯作者：
Hideharu Ishida
中科院分区：
文献类型：
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作者：
Hirotaka Tomida;Takuya Matsuhashi;Hide-Nori Tanaka;Naoko Komura;Hiromune Ando;Akihiro Imamura;Hideharu Ishida
我们发展了一种间接合成α-L-岩藻糖苷的方法。基于L-岩藻糖是6-脱氧-L-半乳糖这一事实，我们的策略包括立体选择性地构建α-L-半乳糖苷并通过C6-脱氧将其转化为α-L-岩藻糖苷。使用4，6-O-二叔丁基亚甲硅烷基（DTBS）保护的L-半乳糖基供体强烈指导α-L-半乳糖苷的形成。DTBS导向的α-L-半乳糖基化反应具有良好的偶联产率和α-选择性，并显示出广泛的底物适用性沿着。在α-L-半乳糖苷的C6-脱氧反应中，Barton-McCombie反应有利于转化为L-岩藻糖苷，产率较高。为了证明我们的方法的适用性，我们合成了天然存在的α-L-岩藻糖苷。
We developed an indirect synthetic method for α-L-fucosides. Based on the fact that L-fucose is 6-deoxy-L-galactose, our strategy consists of the stereoselective construction of α-L-galactoside and its conversion to α-L-fucoside via C6-deoxygenation. The formation of α-L-galactoside is strongly directed using 4,6-O-di-tert-butylsilylene(DTBS)-protected L-galactosyl donors. The DTBS-directed α-L-galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-L-galactosides, the Barton–McCombie reaction facilitated the conversion to L-fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-L-fucosides.