Ni(II)-Catalyzed Regio- and Stereoselective O‑Alkylation for the Construction of 1,2-cis-Glycosidic Linkages

A transition-metal-catalyzed O-alkylation for the regio- and stereoselective construction of 1,2-cis-glycosidic linkages is presented. With nonprecious and readily available Ni­(II) as a catalyst, 1,2-cis-glycosides were obtained via O-alkylation of 1,2-carbohydrate diols that can be accessed in a s...

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Published inOrganic letters Vol. 24; no. 34; pp. 6282 - 6287
Main Authors Feng, Yingle, Guo, Tiantian, Yang, Han, Liu, Guoqiang, Zhang, Qi, Zhang, Shengyong, Chai, Yonghai
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MANNOSYLATION
ACTIVATION
STEREOSPECIFIC SYNTHESIS
MANNOPYRANOSYL
OLIGOSACCHARIDES
1,2-CIS GLYCOSYLATION
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Summary:A transition-metal-catalyzed O-alkylation for the regio- and stereoselective construction of 1,2-cis-glycosidic linkages is presented. With nonprecious and readily available Ni­(II) as a catalyst, 1,2-cis-glycosides were obtained via O-alkylation of 1,2-carbohydrate diols that can be accessed in a small number of steps. The tedious design of protecting groups or anomeric leaving groups could be avoided with this method. The strategy was applied for the efficient preparation of an important commercialized glycosidic compatible solute GG, its derivative MGG, and a branched α-glucan.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02419