Synthesis of glucosamine vinyl ether derivative and its deuterated analog

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Abstract

The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.
Translated title of the contributionСинтез винилового эфира производного глюкозамина и его дейтерированного аналога
Original languageEnglish
Pages (from-to)1401-1404
JournalRussian Chemical Bulletin
Volume69
Issue number7
StatePublished - 2 Sep 2020

Scopus subject areas

  • Organic Chemistry

Keywords

  • calcium carbide
  • vinyl ether
  • glucosamine
  • deuterium labeling
  • vinylation

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