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Issue 8, 2008
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Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside

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Abstract

Dodecyl thioglycosides (3, 4, 5) were prepared by conventional transformation of D-glucose and used as new glycosyl donors for a short-step synthesis of phytoalexin elicitor heptaglucoside. A gentio-tetraoside derivative (6) having three hydroxyl groups was synthesized by NIS–TfOH promoted glycosylate in more than 90% yield followed by selective removal of temporary protective groups. Undesired formation of α-glycosides at the introduction of β-(1→3)-branches into gentio-oligosaccharides was found to be suppressed by use of a thiophilic reagent system, BSP (1-benzenesulfinyl piperidine)–Tf2O, giving the heptaglucoside in only four glycosylation steps.

Graphical abstract: Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside

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Publication details

The article was received on 16 Jan 2008, accepted on 25 Jan 2008 and first published on 22 Feb 2008


Article type: Paper
DOI: 10.1039/B800809D
Citation: Org. Biomol. Chem., 2008,6, 1441-1449
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    Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside

    S. Son, C. Tano, J. Furukawa, T. Furuike and N. Sakairi, Org. Biomol. Chem., 2008, 6, 1441
    DOI: 10.1039/B800809D

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