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Free-radical synthesis of 3-(2-cyanoethyl)- and 3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-Erythro-pentofuranoside and their application in the synthesis of potential antiviral nucleosides

✍ Scribed by Jesper Lau; Krzysztof Walczak; Krzysztof Pupek; Carsten Buch; Carsten M. Nielsen; Erik B. Pedersen

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
621 KB
Volume
324
Category
Article
ISSN
0365-6233

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✦ Synopsis

Free•radical reaction of different carbohydrate eductsZ.5, and 7 withaery-10nibile in the presence of tributyltin hydride and a radicalinitiator (AIBN) gave the methyl 3-(2-cyanoethyl)-2,3-dideoxypentofuranosides 3a and 6. Similar reaction of 2 withmethyl acrylate gave3-(2-methoxycarbonylethyl)-2,3-dideoxypentofuranose 3b. Nucleoside coupling of 3a with silylated uracil gavean anomerlc mixture of l3and (X-nucleoside 8 and 9 which were deproteeted to give 10 and 11. respectively. Similar reaction of 3b with silylated ~-isobutyrylcytosine gave 12 and 13 which were deproteeted to give the final nucleosides 16 and 17. respectively. None of the compounds lOa,11, 14-17showed significant activity against HIV.

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