Synthesis of oligodeoxynucleoside phosphoromonothioates and phosphorodithioates by a phosphotriester method

Article abstract of DOI:10.1080/07328319708006243

A phosphotriester method for the synthesis of dithymidine phosphoromonothioates and phosphorodithioates with new S-protecting groups has been investigated. Four of the S-protecting groups possesed catalytic activity, however side reactions occurred during deprotection. The best S- protecting group was 4-chloro-2-nitrobenzyl which could be removed with a minimum of side reactions (0.3 %). The coupling reagent PyFNOP (14) gave protected dithymidine phosphoromonothioate in 96 % yield after 15 rain coupling. Furthermore PyFNOP chemoselectively activates oxygen in nucleoside phosphorodithioate monomers 9 and can be used for the synthesis of oligodeoxynucleoside phosphorodithioates with mixed base sequences.

Full text of DOI:10.1080/07328319708006243

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Synthesis of Oligodeoxynucleoside
Phosphoro-Monothioates and
Phosphorodithioates by a
Phosphotriester Method
Jan Kehler a , Ask Püschl a & Otto Dahl a
a Department of Chemistry , The H. C. Ørsted Institute,
University of Copenhagen , Universitetsparken 5, DK, 2100,
Copenhagen, Denmark Fax:
Published online: 16 Aug 2006.
To cite this article: Jan Kehler , Ask Püschl & Otto Dahl (1997) Synthesis of Oligodeoxynucleoside
Phosphoro-Monothioates and Phosphorodithioates by a Phosphotriester Method, Nucleosides and
Nucleotides, 16:7-9, 1633-1636, DOI: 10.1080/07328319708006243
To link to this article: http://dx.doi.org/10.1080/07328319708006243
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