Glycosyl Sulfonium Ions as Storable Intermediates for Glycosylations

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• 作者：Toshiki Nokami ; Yuki Nozaki ; Yoshihiro Saigusa ; Akito Shibuya ; Shino Manabe ; Yukishige Ito ; Jun-ichi Yoshida
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：March 18, 2011
• 年：2011
• 卷：13
• 期：6
• 页码：1544-1547
• 全文大小：777K
• 年卷期：v.13,no.6(March 18, 2011)
• ISSN：1523-7052

文摘

Glycosyl sulfonium ions, which serve as persistent glycosyl cation equivalents, were prepared by the addition of diorganosulfides to an electrochemically generated glycosyl triflate. Low-temperature and variable-temperature NMR studies were performed to reveal the structure, stability, and reactivity of glycosyl sulfonium ions. The glycosyl sulfonium ions could be used as storable intermediates for reactions with various glycosyl acceptors including thioglycosides to give the corresponding disaccharides.