Protection-free synthesis of glycosyl dithiocarbamates in aqueous media by using 2-chloroimidazolinium reagent

Gefei Li, Masato Noguchi, Haruka Kashiwagura, Yuuki Tanaka, Kazunari Serizawa, Shin ichiro Shoda

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Glycosyl dithiocarbamates (GDTCs) have been synthesized directly from the corresponding unprotected sugars and dithiocarbamate salts in good yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as condensing agent in aqueous media. The three-component one-pot synthesis of GDTCs starting from unprotected sugars, carbon disulfide, and secondary amines has also been successfully demonstrated. This is the first report on the direct synthesis of GDTCs from unprotected sugars without using any protecting groups.

Original languageEnglish
Pages (from-to)3529-3531
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number31
DOIs
Publication statusPublished - 2016

Keywords

  • 2-Chloro-1,3-dimethylimidazolinium chloride
  • Direct anomeric activation
  • Glycosyl dithiocarbamate
  • Protection-free synthesis
  • Unprotected sugar

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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