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Stereochemistry of internucleotide bond formation by the H-phosphonate method. 7. Stereoselective formation of ribonucleoside (R-P)- and (S-P)-3 '-H-phosphonothioate monoesters
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2010 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 4, 410-419 p.Article in journal (Refereed) Published
Abstract [en]

Ribonucleoside 3'-H-phosphonothioate monoesters exist in the form of (R-P)- and (S-P)-diastereomers. In order to obtain them in good yields and in high stereochemical purity, stereoselective strategies for their preparation were investigated. For the synthesis of the (R-P)-isomer, a stereoselective sulfhydrolysis of an activated nucleoside H-phosphonate was developed, while the monoesters with an (S-P)-configuration were prepared by asymmetric transformation of diastereomeric mixtures of nucleoside 3'-H-phosphonothioates using either a condensation with 9-fluorenemethanol, followed by beta-elimination, or via pivaloylation-hydrolysis reaction sequence. A tentative assignment of the absolute configurations of the obtained diastereomers of 3'-H-phosphonothioate esters was carried out via a stereochemical correlation analysis.

Place, publisher, year, edition, pages
2010. Vol. 21, no 4, 410-419 p.
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-49917DOI: 10.1016/j.tetasy.2010.01.022ISI: 000277825700007OAI: diva2:380259
authorCount :3Available from: 2010-12-21 Created: 2010-12-20 Last updated: 2010-12-21Bibliographically approved

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Stawinski, Jacek
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