With the aim of preparing a library of ion transporters based on a CyPLOS (cyclic phosphate-linked oligosaccharide) backbone, we describe the synthesis of a novel azido-derivatized CyPLOS analogue that is tailored for practical post-synthetic functionalization with a variety of labels. As a prerequisite for the effective preparation of this phosphate-linked macrocycle, the compatibility of azido alcohols as coupling agents in phosphoramidite synthetic protocols was preliminarily investigated in solution by using 31P NMR spectroscopy to monitor the standard coupling of a nucleoside 3'- phosphoramidite with suitable model alcohols and azides.

On the compatibility of azides in phosphoramidite-based couplings: synthesis of a novel, convertible azido-functionalized CyPLOS analogue / Coppola, Cinzia; Simeone, Luca; DE NAPOLI, Lorenzo; Montesarchio, Daniela. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 6:47(2011), pp. 1155-1165. [10.1002/ejoc.201001057]

On the compatibility of azides in phosphoramidite-based couplings: synthesis of a novel, convertible azido-functionalized CyPLOS analogue.

COPPOLA, CINZIA;SIMEONE, LUCA;DE NAPOLI, LORENZO;MONTESARCHIO, DANIELA
2011

Abstract

With the aim of preparing a library of ion transporters based on a CyPLOS (cyclic phosphate-linked oligosaccharide) backbone, we describe the synthesis of a novel azido-derivatized CyPLOS analogue that is tailored for practical post-synthetic functionalization with a variety of labels. As a prerequisite for the effective preparation of this phosphate-linked macrocycle, the compatibility of azido alcohols as coupling agents in phosphoramidite synthetic protocols was preliminarily investigated in solution by using 31P NMR spectroscopy to monitor the standard coupling of a nucleoside 3'- phosphoramidite with suitable model alcohols and azides.
2011
On the compatibility of azides in phosphoramidite-based couplings: synthesis of a novel, convertible azido-functionalized CyPLOS analogue / Coppola, Cinzia; Simeone, Luca; DE NAPOLI, Lorenzo; Montesarchio, Daniela. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 6:47(2011), pp. 1155-1165. [10.1002/ejoc.201001057]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/379791
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