Recent advances in boron-mediated aglycon delivery (BMAD) for the efficient synthesis of 1,2-cis glycosides

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作者
Takahashi, Daisuke [1 ]
Inaba, Kazuki [1 ]
Toshima, Kazunobu [1 ]
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[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama,223-8522, Japan
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Boron; -; Glycosides; Glycosylation; Regioselectivity; Sugars;
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摘要
Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017. © 2022 Elsevier Ltd
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