4.4 Article

Practical heavy fluorous tag for carbohydrate synthesis with minimal chromatographic purification

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 50, Pages 6539-6541

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.10.016

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A practical heavy fluorous tag 5 bound to a benzylic linker was prepared and applied to carbohydrate synthesis. The fluorous tag 5 was readily introduced to the desired hydroxyl group and carboxyl group by using various methods. Synthesis of the oligosaccharide, which included the terminal structure of class III mucin, was achieved with single-column chromatographic purification. In addition, because of the symmetrical structure of 5, each fluorous synthetic intermediate could be analyzed much easier by NMR spectroscopy than in the case of the fluorous compounds connecting our previous fluorous tags. (C) 2010 Elsevier Ltd. All rights reserved.

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