Synthesis of CH 2 -Linked α(1,6)-Disaccharide Analogues by α-Selective Radical Coupling C-Glycosylation

C-Linked carbohydrate structure, in which the cleavable O-glycosidic linkage is replaced by a carbon unit, is a useful tool for functional analyses of glycoconjugates. We describe a synthetic method for α-CH -linked disaccharide structures, such as Glc(1,6)-Glc, by stereoselective radical-coupling C...

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Published inOrganic letters Vol. 21; no. 6; pp. 1588 - 1592
Main Authors Kiya, Noriaki, Hidaka, Yu, Usui, Kazuteru, Hirai, Go
Format Journal Article
LanguageEnglish
Published United States 15.03.2019
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Summary:C-Linked carbohydrate structure, in which the cleavable O-glycosidic linkage is replaced by a carbon unit, is a useful tool for functional analyses of glycoconjugates. We describe a synthetic method for α-CH -linked disaccharide structures, such as Glc(1,6)-Glc, by stereoselective radical-coupling C-glycosylation between a conformationally constrained and stable C1-sp hybridized xanthate donor and a carefully designed acceptor.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00133