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Molecules 2011, 16(5), 3985-3998; doi:10.3390/molecules16053985

Synthesis of a Novel Benzoyl Adenosine Analog Containing a 1, 4-Dioxane Sugar Analog and the Synthesis of a Corresponding Uracil Adenine Dinucleotide

Department of Chemistry, Norwegian University of Science and Technology, 7491 Trondheim, Norway
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Author to whom correspondence should be addressed.
Received: 3 March 2011 / Revised: 28 April 2011 / Accepted: 6 May 2011 / Published: 12 May 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Adenosine analogs in which the sugar unit was replaced by a 1,4-dioxane sugar equivalent, were prepared by coupling the 1,4-dioxane sugar analog as its anomeric acetates, with N6-benzoyl protected adenine. The 1,4-dioxane system was obtained in an enantioselective synthesis from (R,R)-dimethyl tartrate. Using standard phosphorimidite methodology, the adenine analog was further reacted with a 1,4-dioxane uridine analog to give the corresponding, protected dinucleotide, set-up for further condensation into larger oligonucleotides.
Keywords: nucleoside analogs; heterocyclic; adenosine; 1,4-dioxane; uracil-adenine nucleoside analogs; heterocyclic; adenosine; 1,4-dioxane; uracil-adenine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Yu, Q.; Carlsen, P. Synthesis of a Novel Benzoyl Adenosine Analog Containing a 1, 4-Dioxane Sugar Analog and the Synthesis of a Corresponding Uracil Adenine Dinucleotide. Molecules 2011, 16, 3985-3998.

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