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

doi:10.3390/molecules16053985

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

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

Qiang Yu and Per Carlsen*

Department of Chemistry, Norwegian University of Science and Technology, 7491 Trondheim, Norway

* Author to whom correspondence should be addressed.

Received: 3 March 2011; in revised form: 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

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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.

AMA 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(5):3985-3998.

Chicago/Turabian Style

Yu, Qiang; Carlsen, Per. 2011. "Synthesis of a Novel Benzoyl Adenosine Analog Containing a 1, 4-Dioxane Sugar Analog and the Synthesis of a Corresponding Uracil Adenine Dinucleotide." Molecules 16, no. 5: 3985-3998.

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