Kinetically Controlled Fischer Glycosidation under Flow Conditions: A New Method for Preparing Furanosides

Seiji Masui, Yoshiyuki Manabe, Kohtaro Hirao, Atsushi Shimoyama, Takahide Fukuyama, Ilhyong Ryu, Koichi Fukase*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Kinetically controlled Fischer glycosidation was achieved under flow conditions. β-Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) was used as an acid catalyst. This reaction directly converted aldohexoses into kinetically favored furanosides to enable the practical synthesis of furanosides. After optimization of the reaction temperature and residence time, glucofuranosides, galactofuranosides, and mannofuranosides were synthesized in good yields.

Original languageEnglish
Pages (from-to)397-400
Number of pages4
JournalSynlett
Volume30
Issue number4
DOIs
StatePublished - 1 Jan 2019

Keywords

  • Fischer glycosidation
  • carbohydrate
  • flow chemistry
  • furanosides
  • kinetically controlled reaction
  • supported catalysis

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