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: [email protected]
,
Janusz Jurczak*
b  Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 03 February 2015

Accepted after revision: 13 April 2015

Publication Date:
08 May 2015 (online)


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%.

Supporting Information

 
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