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Synthesis 2008(6): 913-916  
DOI: 10.1055/s-2008-1032198
PAPER
© Georg Thieme Verlag Stuttgart · New York

Towards Sucrose Macrocycles with Higher Symmetry via a ‘Click Chemistry’ Route

Sławomir Jarosz*, Bartosz Lewandowski, Arkadiusz Listkowski
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: sljar@icho.edu.pl;
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Publication History

Received 16 November 2007
Publication Date:
28 February 2008 (online)

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Abstract

Chiral macrocycles containing the sucrose skeleton were prepared by a ‘click chemistry’ route. The substrate for the Huisgen reaction was obtained from sucrose in eight steps. The 1,3-dipolar cycloaddition yielded the intramolecular as well as the C 2-symmetric macrocycles. Optimization of the reaction conditions allowed the preparation of both types of adducts with high selectivity and in good yields.

Key words

sucrose - receptors - complexation - click chemistry

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15

Although it is known that the Huisgen reaction (without catalyst) usually provides a mixture of the 1,4- and 1,5-triazoles reaction of sucrose synthon 6 with or without catalyst gave the same product.

16

The yields are reported for isolated compounds. In all reactions we have observed significant amounts of tars resulting (most likely) from the linear polymerization of the monomer 6.