AI Article Synopsis
- The study presents a synthetic method for creating 1'-C-branched N,O-nucleosides using 1,3-dipolar cycloaddition with ethoxycarbonylnitrone.
- An asymmetric version of the process utilizes a chiral auxiliary at the nitrone's carbon, enhancing the efficiency of the reaction.
- This approach successfully produces beta-D and beta-L nucleosides in good yields, showcasing its potential in nucleoside synthesis.
Article Abstract
A synthetic approach towards 1'-C-branched N,O-nucleosides is reported, based on 1,3-dipolar cycloaddition of ethoxycarbonylnitrone. The asymmetric version of the process exploits the presence of a chiral auxiliary at the carbon atom of nitrone and leads to beta-D and beta-L nucleosides in good yields.
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| http://dx.doi.org/10.1081/NCN-120022623 | DOI Listing |
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Diastereo- and enantioselective synthesis of 1'-C-branched N,O-nucleosides.
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Article Synopsis
- The study presents a synthetic method for creating 1'-C-branched N,O-nucleosides using 1,3-dipolar cycloaddition with ethoxycarbonylnitrone.
- An asymmetric version of the process utilizes a chiral auxiliary at the nitrone's carbon, enhancing the efficiency of the reaction.
- This approach successfully produces beta-D and beta-L nucleosides in good yields, showcasing its potential in nucleoside synthesis.
Stereoselective synthesis of 1'-C-branched arabinofuranosyl nucleosides via anomeric radicals generated by 1,2-acyloxy migration.
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School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan
Stereoselective C-C bond formation at the anomeric position of uracil and adenine nucleoside has been accomplished through reaction of the anomeric radical, generated by 1,2-acyloxy migration, with a radical acceptor. The present method consists of the following steps: (1) electrophilic addition (bromo-pivaloyloxylation) to 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-protected 1',2'-unsaturated nucleoside, (2) tin radical-mediated reaction of the resulting adduct with a radical acceptor. The use of allyl(tributyl)tin gave the 1'-C-allylated uracil nucleoside 14 in 66% yield together with the unrearranged 2'-C-allylated product 15 (6%).
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