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

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Author

  • Jenny Ågren
  • Johan Billing
  • Hans Grundberg
  • Ulf Nilsson

Summary, in English

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.

Publishing year

2006

Language

English

Pages

3141-3145

Publication/Series

Synthesis

Issue

18

Document type

Journal article

Publisher

Oxford Polytechnic, Oxford

Topic

  • Organic Chemistry

Keywords

  • carbohydrates
  • macrocycles
  • cycloadditions
  • azides
  • amino acids

Status

Published

ISBN/ISSN/Other

  • ISSN: 0039-7881