Development of one step synthesis of glycosyl acceptor substituted by overcrowded silyl group and regioselective glycosidation at 3-OH

• Project/Area Number: 25410170
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Bio-related chemistry
• Research Institution: Saitama University
• Principal Investigator: HATANO Ken 埼玉大学, 理工学研究科, 准教授 (40332316)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
• Keywords: シリル基 / グリコシル化 / 位置選択的 / 糖鎖合成 / グリコシリ化 / シアリルラクトース / シアル酸 / 立体障害 / 速度論的反応 / 嵩高いケイ素置換基 / 糖水酸基 / 速度論的保護 / 位置選択的グリコシル化 / オリゴ糖合成

Outline of Final Research Achievements

Silylation of hydroxyl groups on monosaccharides and lactose were obtained in good yield by one step reaction. In the case of lactose, the silylation occurred on 6, 2' and 6' positions of hydroxyl groups and the trisilylated lactose was able to isolate by recrystallization. Regioselective glycosydation at 3-OH (however 3'-OH in the case of lactose) of the silylated saccharides with a glucose derivative as a glycosyl donor were observed.

Research Products

• [Presentation] Regioselective glycosylation with silylated saccharide acceptor (2016)
  • Author(s): Ryo Ito, Takuma Matsumoto, Ryuhei Konose, Tetsuo Koyama, Koji Matsuoka, and Ken Hatano
  • Organizer: CEMS International Symposium on Supramolecular Chemistry and Functional Materials 2016
  • Place of Presentation: 東京大学（東京都・文京区）
  • Year and Date: 2016-01-13
  • Int'l Joint Research
• [Presentation] Oligosaccharides synthesis using silicon bulky protecting group (2015)
  • Author(s): Takuma Matsumoto, Ryo Ito, Ryuhei Konose, Tetsuo Koyama, Koji Matsuoka, and Ken Hatano
  • Organizer: 2015 環太平洋国際化学会議 (PACIFICHEM 2015)
  • Place of Presentation: ハワイコンベンションセンター, Hawaii（アメリカ）
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] 嵩高いケイ素置換基を保護基として用いたオリゴ糖合成 (2015)
  • Author(s): 松本 拓磨・伊藤 諒・神瀬 龍平・小山 哲夫・松岡 浩司・幡野 健
  • Organizer: 日本化学会第95春季年会(2015)
  • Place of Presentation: 日本大学 船橋キャンパス
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] ケイ素保護糖受容体の位置選択的グリコシル化 (2015)
  • Author(s): 伊藤 諒・松本 拓磨・神瀬 龍平・小山 哲夫・松岡 浩司・幡野 健
  • Organizer: 日本化学会第95春季年会(2015)
  • Place of Presentation: 日本大学 船橋キャンパス
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] かさ高いシリル基のオリゴ糖合成への利用 (2013)
  • Author(s): 神瀬龍平、高畑徳允、伊藤諒、小山哲夫、松岡浩司、幡野健
  • Organizer: 第17回ケイ素化学協会シンポジウム
  • Place of Presentation: 箱根湯本温泉ホテルおかだ（箱根）