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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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Title: Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside
Authors: Son, Sang-Hyun Browse this author
Tano, Chiharu Browse this author
Furukawa, Jun-ichi Browse this author
Furuike, Tetsuya Browse this author
Sakairi, Nobuo Browse this author →KAKEN DB
Keywords: Glycosylation
Synthesis
Branched Oligosaccharide
Phytoalexin-elicitor
Dodecyl thioglycoside
グリコシル化反応
合成
分枝オリゴ糖
ファイトアレキシンエリシター
ドデシルチオグリコシド
Issue Date: Apr-2008
Publisher: Royal Society of Chemistry
Journal Title: Organic & Biomolecular Chemistry
Volume: 6
Issue: 8
Start Page: 1441
End Page: 1449
Publisher DOI: 10.1039/b800809d
PMID: 18385851
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% yields followed by selective removal of temporary protective groups. Undesired formation of α-glycosides in 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.
Rights: Org. Biomol. Chem., 2008, 6(8), pp.1441-1449 - Reproduced by permission of The Royal Society of Chemistry (RSC)
Type: article (author version)
URI: http://hdl.handle.net/2115/38386
Appears in Collections:環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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