Title: Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation.
Authors: Ling, Jesse; Bennett, Clay S.
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.
Subjects: NATURAL products; DISACCHARIDES; GLYCOCONJUGATES; SULFONATES; SULFONYL chlorides
Publication: Angewandte Chemie, 2020, Vol 132, Issue 11, p4334
ISSN: 0044-8249
Publication type: Academic Journal
DOI: 10.1002/ange.201914221

Versatile Glycosyl Sulfonates in β‐Selective C‐Glycosylation.

Ling, Jesse; Bennett, Clay S.