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

• Son, Sang-Hyun

• Tano, Chiharu

• Furukawa, Jun-ichi

• Furuike, Tetsuya

• Sakairi, Nobuo

抄録

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.

収録刊行物

• Organic & Biomolecular Chemistry

  Organic & Biomolecular Chemistry 6 (8), 1441-1449, 2008-04

  Royal Society of Chemistry

キーワード

• グリコシル化反応
• 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

詳細情報

• CRID: 1050845763931017728
• NII論文ID: 120001253410
• NII書誌ID: AA1168650X
• HANDLE: 2115/38386
• ISSN: 14770520
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles