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.
Highlights
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]
In this communication we wish to report our recent findings dealing with the synthesis of adenosine analogs 2a and 2b, which as the N-benzoyl protected compounds were tested in dinucleotide formation with uridines 1a
All the tartrate stereoisomers are readily available from the chiral pool, conveniently allowing for the synthesis of all the possible stereoisomers of the nucleoside analogs
Summary
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 The sugar unit has for example been replaced by a 1,4-dioxane moiety [2,3,4,5,6] Some of these structures were reported to exhibit interesting biological activities [2,3], which may be ascribed to their particular flexible conformational properties [4]. 1a or 1b where the sugar was substituted by an optically active 1,4-dioxane moiety [7] These uridine analog was further elaborated into the corresponding dinucleotide using standard phosphorimidite. We reported [7] that preparation of the related adenosine analog failed In this communication we wish to report our recent findings dealing with the synthesis of adenosine analogs 2a and 2b, which as the N-benzoyl protected compounds were tested in dinucleotide formation with uridines 1a
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