An efficient convergent synthesis of adenosine-5'-N-alkyluronamides

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Abstract

Herein we report an efficient synthesis of adenosine-5 -N-alkyluronamides in which an enzyme-mediated deacetylation reaction is a key to the selective modification of the 5 -N-position, prior to coupling the ribose and purine components via a microwave-assisted Vorbruggen coupling. This approach provides access to highly functionalised adenosines with 2- and N-6-substitutents, which can be incorporated before or after the ribose-coupling step. In all cases the microwave-assisted Vorbruggen coupling conditions afforded anomerically pure purine ribosides in good to excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1772 - 1777
Number of pages6
JournalTetrahedron
Volume64
Issue number8
Publication statusPublished - 2008

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