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Issue 14, 2003
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An easy access to halide ion-catalytic α-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents

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Abstract

The reaction of a 2-O-benzyl-1-hydroxy sugar with CBr4 and Ph3P generates a glycosyl bromide in situ, which is coupled with an acceptor alcohol in the presence of N,N-tetramethylurea to afford an α-glycosyl product virtually quantitatively. In a proposed pathway, the reagent combination plays multiple roles such as the generation of a glycosyl donor, the activation of glycosylation, and the dehydration of the reaction system. These roles allow a simple α-glycosylation to be performed without special attention to dehydration. Various α-glycosyl (D-gluco-, D-galacto- and L-fuco-) products including glycosyl glycerols and cholesterols have been prepared with this method.

Graphical abstract: An easy access to halide ion-catalytic α-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents

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Publication details

The article was received on 14 Apr 2003, accepted on 03 Jun 2003 and first published on 18 Jun 2003


Article type: Paper
DOI: 10.1039/B303984F
Citation: Org. Biomol. Chem., 2003,1, 2518-2521

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    An easy access to halide ion-catalytic α-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional reagents

    Y. Shingu, Y. Nishida, H. Dohi and K. Kobayashi, Org. Biomol. Chem., 2003, 1, 2518
    DOI: 10.1039/B303984F

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