Preparation of C-glycoside pendant β[2]- and β[2,2]-amino acids

• Yoko Inaba

• Shigenobu Yano

• Yuji Mikata

Bibliographic Information

Other Title

• Preparation of C glycoside pendant v 2 and v 2 2 amino acids

Abstract

Facile preparations of C-glycosyl β2- and β2,2-amino acids are described. Selective formation of a β-C-glycoside linkage was achieved by the reaction of a 2,3,4,6-tetra-O-acetyl-α-d-gluco/galactopyranosyl bromide (α-acetobromoglucose/galactose) with the carbanion of a cyanoacetate ester. Crystallization selectively afforded one of two diastereomers with respect to the chiral center at the α-carbon of the side chain (C-2), however, this compound was found to epimerize during the following nitrile reduction. Separation of the diastereomers was achieved via the Fmoc derivatives. Diastereomerically pure C-glycosyl β2,2-amino acids were prepared by diastereoselective alkylation of C-glycosylated enolate, followed by nitrile hydrogenation. The present procedure serves as an efficient route to C-glycosylated β-amino acids containing a non-biodegradable linkage.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 81 (5), 606-616, 2008

  Tokyo : Chemical Society of Japan

Keywords

• General Chemistry

Details

• CRID: 1520854805509026944
• NII Article ID: 10021075522
• NII Book ID: AA00580132
• ISSN: 00092673
• ISSN: 13480634
• DOI: 10.1246/bcsj.81.606
• NDL BIB ID: 9489811
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9489811
• Web Site: https://academic.oup.com/bcsj/article-pdf/81/5/606/56270045/bcsj.81.606.pdf
• Text Lang: en
• NDL Source Classification:
  • ZP1(科学技術--化学・化学工業)
• Data Source:
  • NDL
  • Crossref
  • CiNii Articles