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However, the intricate stereochemistry and densely packed functional groups of carbohydrates pose significant challenges for precise stereoselectivity and regioselectivity control. Herein, we report a palladium\u2010catalyzed, stereospecific, and ligand\u2010controlled regiodivergent glycosyl Suzuki\u2013Miyaura coupling of 3\u2010boryl\u2010glycals, establishing a robust platform for glycoside diversification with versatile C1 and C3 modification. Notably, stable 3\u2010boryl\u2010glycals with 1,1,2,2\u2010tetraethylethylene glycol protection were first synthesized and fully characterized. Operating under mild conditions, this reaction enables the efficient synthesis of diverse 2,3\u2010unsaturated aryl\/alkenyl <jats:italic>C<\/jats:italic>\u2010glycosides with exceptional regio\u2010 and stereoselectivity. 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