SYNTHESIS OF NOVEL 3-[(1-GLYCOSYL-1<i>H</i>-1,2,3-TRIAZOL-4-YL)- METHYLAMINO]KET-2-EN-1-ONES

Авторы

  • Ashok K. Prasad Department of Chemistry University of Delhi Delhi
  • Banty Kumar a) Department of Chemistry University of Delhi Delhi b) Rajdhani College Department of Chemistry University of Delhi Delhi
  • Jyotirmoy Maity Department of Chemistry University of Delhi Delhi
  • Amit Kumar Department of Chemistry University of Delhi Delhi
  • Vinod Khatri Department of Chemistry University of Delhi Delhi
  • Bhawani Shankar Deshbandhu College University of Delhi

DOI:

https://doi.org/10.1007/4388

Ключевые слова:

N-glycoconjugates, CuAAC reaction, Sonogashira reaction

Аннотация

Nine 3-[(1-β-D-ribofuranosyl- and 3-[(1-β-D-glucopyranosyl-1H-1,2,3-triazol-4-yl)methylamino]ket-2-en-1-ones have been synthesized by copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction between propargylamine derivatives and 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose or 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, followed by deprotection of the resulting tri-O-benzoyl- or tetra-O-acetyl-1-β-D-glycosyltriazoles in good yields. The precursor propargylamine derivatives were synthesized by Sonogashira reaction of substituted acetylenes and benzoyl chloride followed by Michael-type addition of propargylamine to the resulting substituted alkynes in good yields. The precursor azido sugars, 1-azido-2,3,5-tri-O-benzoyl-β-D-ribofuranose and 2,3,4,6-tetra-O-acetyl-1-azido-β-D-glucopyranose, were synthesized by azidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and β-D-glucopyranose pentacetate, respectively, with azidotrimethylsilane in the presence of tin(IV) chloride. All products were unambiguously characterized on the basis of the spectral data analysis.

Биографии авторов

Ashok K. Prasad, Department of Chemistry University of Delhi Delhi

Professor

Department of Chemistry

University of Delhi

Delhi

India

Banty Kumar, a) Department of Chemistry University of Delhi Delhi b) Rajdhani College Department of Chemistry University of Delhi Delhi

Assistant Professor

Jyotirmoy Maity, Department of Chemistry University of Delhi Delhi

Assistant Professor

Amit Kumar, Department of Chemistry University of Delhi Delhi

Research Scholar

Vinod Khatri, Department of Chemistry University of Delhi Delhi

Research Scholar

Bhawani Shankar, Deshbandhu College University of Delhi

Assistant Professor

Загрузки

Опубликован

2018-05-15