Modular Stereoselective Synthesis of (1→2)‐C‐Glycosides based on the sp2–sp3 Suzuki–Miyaura Reaction |
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| Authors: | Beata Oroszova Jan Choutka Dr Radek Pohl Dr Kamil Parkan |
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| Affiliation: | 1. Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague 6 (Czech Republic);2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v. v. i. Flemingovo nám. 2, 166 10 Prague 6 (Czech Republic) |
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| Abstract: | This work reports a modular and rapid approach to the stereoselective synthesis of a variety of α‐ and β‐(1→2)‐linked C‐disaccharides. The key step is a Ni‐catalyzed cross‐coupling reaction of D ‐glucal pinacol boronate with alkyl halide glycoside easily prepared from commercially available D ‐glucal. The products of this sp2–sp3 cross‐coupling reaction can be converted to glucopyranosyl, mannopyranosyl, or 2‐deoxy‐glucopyranosyl C‐mannopyranosides by one‐ or two‐step stereoselective oxidative–reductive transformations. To the best of our knowledge, we demonstrated the first synthetic application of a challenging sp2–sp3 Suzuki‐Miyaura cross‐coupling reaction in carbohydrate chemistry. |
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| Keywords: | C‐disaccharides C‐glycosides diastereoselectivity Mitsunobu reaction sp2– sp3 coupling |
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