期刊
CHEMICAL SCIENCE
卷 13, 期 6, 页码 1600-1607出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc05772c
关键词
-
资金
- National Natural Science Foundation of China [21977039, 21877055, 21762024, 22007039, 21867012]
The new glycosylation system utilizes a charged thiourea hydrogen-bond-donor catalyst and PTFAI donors, showing broad substrate scope, stereoselectivity, and good yields. The mild catalysis conditions make it suitable for synthesizing challenging phenolic glycosides and a chemoselective glycosylation procedure.
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.
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