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Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation

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Abstract

We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener.

Graphical abstract: Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation

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Article information


Submitted
31 Jan 2020
Accepted
16 Mar 2020
First published
17 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation

Y. Hidaka, N. Kiya, M. Yoritate, K. Usui and G. Hirai, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00785D

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