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Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation
Authors:Jesse Ling  Clay S. Bennett
Abstract:C‐Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results in the stereospecific construction of β‐linked C‐glycosides. This reaction tolerates a range of acceptors and donors, including disaccharides. The resulting products can be readily derivatized into C‐glycoside analogues of β‐glycoconjugates, including C‐disaccharide mimetics.
Keywords:carbohydrates  C-glycosides  glycoconjugates  glycosylation  glycosyl sulfonates
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