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Hokkaido University Collection of Scholarly and Academic Papers >
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Stereoselective tris-glycosylation to introduce β-(1→3)-branches into gentiotetraose for the concise synthesis of phytoalexin-elicitor heptaglucoside
| 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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Submitter: 坂入 信夫
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