exo-N-[2-(4-Azido-2,3,5,6-tetrafluorobenzamido)ethyl]-dC: a novel intermediate in the synthesis of dCTP derivatives for photoaffinity labelling

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Unit:
Department of Chemistry
Title:
exo-N-[2-(4-Azido-2,3,5,6-tetrafluorobenzamido)ethyl]-dC: a novel intermediate in the synthesis of dCTP derivatives for photoaffinity labelling
Languages of Item:
English
Abstract:
An alternative route for the synthesis of a photoaffinity labelling (PAL) dCTP derivative is reported. This method involves the intermediacy of exo-N-[2-(4-azido-2,3,5,6-tetrafluorobenzamido)ethyl]-dC. The latter is prepared from the coupling of known N-(2-aminoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, prepared in an improved three-step sequence, with an activated 4-triazolyl derivative of dU, followed by deprotection. 19F NMR spectroscopy proved extremely useful in following the synthetic transformations, and enabled control of any adventitious reduction of the azides. 2007 Elsevier Ltd. All rights reserved.
Publication year:
2008
Authors:
Crina Cismas
Thanasis Gimisis
Journal:
TETRAHEDRON LETTERS
Publisher:
ELSEVIER BV
Volume:
49
Number:
8
Pages:
1336--1339
Keywords:
3,5,6-tetrafluorobenzamide derivatives,[4-Azido-2
Main subject category:
Science
DOI:
10.1016/j.tetlet.2007.12.083
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