Reaction products from Fischer's methylation of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)

  • Toshitsugu Kai
  • , Xue Sun
  • , Makoto Tanaka
  • , Hiroaki Takayanagi
  • , Kimio Furuhata

Research output: Contribution to journalArticlepeer-review

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Abstract

Several compounds were isolated from the Fischer's methylation reaction mixture of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) with hydrochloric acid or methanesulfonic acid in methanol. The major product was methyl (methyl 3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate (2), which we have already reported. New furan derivatives and a 4,8-anhydro product were also isolated. The structures of these compounds were elucidated by nuclear magnetic resonance spectroscopy and X-ray cristallographic analysis.
Original languageEnglish
Pages (from-to)208-211
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume44
Issue number1
DOIs
StatePublished - Jan 1 1996

Keywords

  • 4,8-anhydro product
  • Crystalline KDN
  • Fischer's glycosylation
  • Furan derivative
  • Sialic acid
  • β-elimination

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