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Synthesis 2015; 47(13): 1838-1843
DOI: 10.1055/s-0034-1380701
psp
© Georg Thieme Verlag Stuttgart · New York

Improved Synthesis of C2 and C6 Monoderivatives of α- and β-Cyclodextrin via the Click Chemistry Approach

Kazimierz Chmurski
a   Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
,
Pawel Stepniak
a   Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
b   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   eMail: jurczak@icho.edu.pl
,
Janusz Jurczak*
b   Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   eMail: jurczak@icho.edu.pl
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Publikationsverlauf

Received: 03. Februar 2015

Accepted after revision: 13. April 2015

Publikationsdatum:
08. Mai 2015 (online)

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Abstract

An efficient multigram-scale azide-alkyne coupling of cyclodextrin derivatives mono-6-azido-6-deoxy-β-cyclodextrin, mono-2-O-propargyl-β-cyclodextrin, and mono-2-O-propargyl-α-cyclodextrin with terminal alkynyl aryl ethers or azides, mediated by copper(I) is reported. This process uses a stoichiometric ratio of substrates and 5 mol% of the copper catalyst to give the products with full conversion; thus, no chromatographic purification is necessary. The yields of both α- and β-cyclodextrin derivatives are in the range of 80 to 99%.

Key words

cyclodextrins - azides - copper - cycloaddition - ligands

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380701.
  • Supporting Information
 

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