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Hydrogen bond activated glycosylation under mild conditions.
- Source :
-
Chemical science [Chem Sci] 2021 Dec 15; Vol. 13 (6), pp. 1600-1607. Date of Electronic Publication: 2021 Dec 15 (Print Publication: 2022). - Publication Year :
- 2021
-
Abstract
- Herein, we report a new glycosylation system for the highly efficient and stereoselective formation of glycosidic bonds using glycosyl N -phenyl trifluoroacetimidate (PTFAI) donors and a charged thiourea hydrogen-bond-donor catalyst. The glycosylation protocol features broad substrate scope, controllable stereoselectivity, good to excellent yields and exceptionally mild catalysis conditions. Benefitting from the mild reaction conditions, this new hydrogen bond-mediated glycosylation system in combination with a hydrogen bond-mediated aglycon delivery system provides a reliable method for the synthesis of challenging phenolic glycosides. In addition, a chemoselective glycosylation procedure was developed using different imidate donors (trichloroacetimidates, N -phenyl trifluoroacetimidates, N -4-nitrophenyl trifluoroacetimidates, benzoxazolyl imidates and 6-nitro-benzothiazolyl imidates) and it was applied for a trisaccharide synthesis through a novel one-pot single catalyst strategy.<br />Competing Interests: The authors declare no conflict of interest.<br /> (This journal is © The Royal Society of Chemistry.)
Details
- Language :
- English
- ISSN :
- 2041-6520
- Volume :
- 13
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Chemical science
- Publication Type :
- Academic Journal
- Accession number :
- 35282639
- Full Text :
- https://doi.org/10.1039/d1sc05772c