通过还原性 C(sp2)-C(sp3)交叉偶联反应立体选择性合成 C-芳基-α-糖苷

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett Pub Date : 2024-07-19 DOI:10.1055/a-2352-4760

Noyuri Kudo, Suzuka Chiba, Shunsuke Ono, Masataka Nagatoishi, Makoto Yoritate, Satoru Karasawa, Kazuteru Usui, Go Hirai

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引用次数: 0

摘要

C 芳基苷作为具有生物活性的天然产物和药物发现中的 O 芳基苷模拟物引起了人们的极大兴趣。在此，我们介绍了一种通过光氧化/Ni 双催化剂在溴化糖基和芳基溴之间进行还原交叉偶联而直接合成 C 芳基糖苷的方法。这种方法可实现 C-芳基糖苷、半乳糖苷和甘露糖苷的高α-严格选择性合成。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction

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Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction

C-Aryl glycosides have attracted considerable interest as biologically active natural products and as O-aryl glycoside mimetics in drug discovery. Here, we describe a straightforward synthesis of C-aryl glycosides by photoredox/Ni dual-catalyzed reductive cross-coupling between glycosyl bromides and aryl bromides. This methodology enables a highly α-stereoselective synthesis of C-aryl glucosides, galactosides, and mannosides.

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来源期刊

Synlett 化学-有机化学

CiteScore

3.40

自引率

5.00%

发文量

369

审稿时长

1 months

期刊介绍： SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.