Synthesis and application of novel carbohydrate-based ammonium and triazolium salts

Tamás Nemcsok, Zsolt Rapi, Péter Bagi, P. Bakó

Research output: Contribution to journalArticle

Abstract

The synthesis of nine new carbohydrate-based quaternary ammonium salts and two new triazolium salts starting from d-glucose has been accomplished. Our synthesis utilized the regio- and stereoselective ring opening reaction of 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. In these new types of phase transfer catalysts, the ammonium and triazolium functions are directly attached to the carbohydrate scaffold in different positions (2-, 3-, 6-positions of the sugar). The efficiency of the altrose- and glucose-based quaternary salts were tested in the alkylation of N-(diphenyl) methylene glycine tert-butyl ester with benzyl bromide. To our knowledge this is the first example when sugar-based quaternary ammonium or triazolium salts were used successfully as phase transfer catalysts. The enantiomeric recognition ability of the synthesized salts towards racemic Mosher’s acid silver salt was also investigated by 19F NMR spectroscopy.

Original languageEnglish
JournalSynthetic Communications
DOIs
Publication statusPublished - Jan 1 2019

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Ammonium Compounds
Salts
Carbohydrates
Sugars
Glucose
Catalysts
Alkylation
Silver
Scaffolds
Nuclear magnetic resonance spectroscopy

Keywords

  • Carbohydrate-based quaternary salts
  • enantiomeric recognition
  • phase transfer catalysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and application of novel carbohydrate-based ammonium and triazolium salts. / Nemcsok, Tamás; Rapi, Zsolt; Bagi, Péter; Bakó, P.

In: Synthetic Communications, 01.01.2019.

Research output: Contribution to journalArticle

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