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Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation
Author(s) -
Ling Jesse,
Bennett Clay S.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914221
Subject(s) - chemistry , glycosyl , glycoside , glycosylation , disaccharide , glycoconjugate , hemiacetal , sulfonate , stereochemistry , stereospecificity , organic chemistry , combinatorial chemistry , biochemistry , catalysis , sodium
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.