synthesis of a novel benzoyl adenosine analog containing a 1, 4-dioxane sugar analog and the synthesis of a corresponding uracil adenine dinucleotide合成一种新型的苯甲酰腺苷模拟包含1、恶烷糖模拟和一个相应的尿嘧啶腺嘌呤二核苷酸的合成.pdfVIP

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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合成一种新型的苯甲酰腺苷模拟包含1、恶烷糖模拟和一个相应的尿嘧啶腺嘌呤二核苷酸的合成.pdf

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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合成一种新型的苯甲酰腺苷模拟包含1、恶烷糖模拟和一个相应的尿嘧啶腺嘌呤二核苷酸的合成

Molecules 2011, 16, 3985-3998; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article 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; E-Mail: per.carlsen@chem.ntnu.no; Tel.: +47 Received: 3 March 2011; in revised form: 28 April 2011 / Accepted: 6 May 2011 / Published: 12 May 2011 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 1. Introduction Pursuing development of new antiviral and antitumor agents, a number of new nucleosides analogs have been synthesized in which of the sugar structures were modified [1]. The sugar unit has for example been replaced by a 1,4-dioxane moiet