Glycosylation from the Non-reducing End Using a Combination of Thioglycoside and Glycosyl Sulfoxide as the Glycosyl Donor and the Acceptor

• Kajimoto Tetsuya

  Osaka University of Pharmaceutical Sciences

• Arimitsu Kenji

  Kyoto Pharmaceutical University

• Ozeki Minoru

  Kyoto Pharmaceutical University

• Node Manabu

  Kyoto Pharmaceutical University

Abstract

A glycosylation reaction was performed using a combination of thioglycoside and glycosyl sulfoxide, which were prepared with odorless p-octyloxybenzenethiol, as a glycosyl donor and an acceptor, respectively. Promising results were obtained when p-octyloxylphenyl N-phthaloyl-D-thio-glucosaminide was activated with N-iodosuccinimide (NIS) and triflic acid (TfOH) for glycosylation of the hydroxyl group of the C-6 position of derivatives of D-glucosyl sulfoxide. Successive reduction of the resulting disaccharyl sulfoxides provided the corresponding thioglycosides, which could be used as the glycosyl donors in another glycosylation reaction to afford trisaccharides in good yield. The present method would be useful for the block synthesis of glycosyl donors in the total synthesis of blanched oligosaccharides, especially when N-acetylglucosamines are presented at the non-reducing ends.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 58 (5), 758-764, 2010

  The Pharmaceutical Society of Japan

Keywords

• glycosylation
• glycosyl sulfoxide
• thioglycoside
• odorless benzenethiol

Details

• CRID: 1390001204171854208
• NII Article ID: 130000255844
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.58.758
• COI: 1:STN:280:DC%2BC3czivVGnsQ%3D%3D
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 10661867
• PubMed: 20460812
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10661867
• Web Site: http://www.jstage.jst.go.jp/article/cpb/58/5/58_5_758/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed