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Oxidative Coupling of H-Phosphonate and H-Phosphonothioate Diesters: Iodine as a Reagent and a Catalyst
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2002 (English)In: Collection Symposium Series, Vol. 5, 87-92 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, , 2002. Vol. 5, 87-92 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
URN: urn:nbn:se:su:diva-23242OAI: diva2:190888
Part of urn:nbn:se:su:diva-203Available from: 2004-08-19 Created: 2004-08-19 Last updated: 2010-01-05Bibliographically approved
In thesis
1. Studies on Oxidative Couplings in H-Phosphonate Chemistry
Open this publication in new window or tab >>Studies on Oxidative Couplings in H-Phosphonate Chemistry
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In this thesis oxidative coupling of H-phosphonate and H phosphonothioate diesters with different alcohols and amines are presented. Since the reactions with alcohols previously have been particularly unfavourable due to competing side reactions, a modified protocol leading to high coupling yields of structurally diverse hydroxylic components was developed. The phosphorylation reaction was studied using 31P NMR spectroscopy and for the first time the previously only postulated reactive intermediate involved in these reactions was observed.

The use of iodine in combination with a bulky chlorosilane in pyridine was found to have a profound effect on both the suppression of side reactions and the rate of the oxidative couplings, and led to a clean formation of phosphorylated products in high yields. This synthetic protocol was then extended to include coupling reactions with bis-functional reagents containing hexamethylene linkers to provide handles for derivatisations of oligonucleotides.

A synthetic protocol consisting of the stereospecific oxidative coupling of amines with H-phosphonate diesters to produce phosphoroamidates was designed in such a way that it permitted control of the stereochemical outcome of the reactions.

Based on a silylation-mediated reaction utilising phenyl H phosphonothioate monoester as a thiophosphonyl transferring agent, a method was developed and used for the preparation of H-phosphonothioate building blocks for the synthesis of DNA analogues.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2004. 42 p.
oxidative coupling, H-phosphonate, H-phosphonothioate, organisk kemi
National Category
Organic Chemistry
urn:nbn:se:su:diva-203 (URN)91-7265-934-3 (ISBN)
Public defence
2004-09-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Available from: 2004-08-19 Created: 2004-08-19Bibliographically approved

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