期刊
CHINESE CHEMICAL LETTERS
卷 34, 期 4, 页码 -出版社
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2022.107754
关键词
Hydrogen bond; Glycolipid; Natural product; O-Glycosylation; ?-Selectivity
A hydrogen bond-assisted alpha-selective glycosylation reaction using DBT B-glycosyl donors was developed for constructing 1,2-cis -alpha-glycosidic bond efficiently in natural products. This method was successfully applied to directly synthesize complex oligosaccharide-derived glycolipids with simple protecting chemistry. Mechanistic studies using NMR spectroscopy and DFT calculation supported the concept of hydrogen bond-assisted glycosylation reaction for alpha-specific construction of O-glycosidic linkage.
A hydrogen bond-assisted alpha-selective glycosylation reaction by using 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) ,B-glycosyl donors was developed for the efficient construction of 1,2-cis -alpha-glycosidic bond in nat-ural products. This method was applied successfully to the direct synthesis of complex oligosaccharide-derived glycolipids with simple protecting chemistry. Mechanistic studies using the NMR spectroscopy and DFT calculation provide a proof of concept for hydrogen bond-assisted glycosylation reaction towards alpha-specific construction of O-glycosidic linkage.(c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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