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Synthesis of a chiral and fluorescent sugar-based macrocycle by 1,3-dipolar cycloaddition

Authors
Publisher
Thieme
Publication Date
Keywords
  • Macrocycles
  • Carbohydrates
  • Cycloadditions
  • Azides
  • Amino Acids
  • Chemistry

Abstract

An efficient and modular synthesis of a chiral, amphiphilic, and fluorescent macrocycle is described. A bis-acetylene was prepared by coupling the amino group of a sugar delta-amino acid with a glutamic acid propargylic amide derivative, followed by coupling of the sugar delta-amino acid carboxy group with a glutamic acid propiolyl amide. The bis-acetylene was reacted with 9,10-bis(azidomethyl)anthracene under Cu(I) catalysis to afford the target fluorescent macrocycle.

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