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Towards synthesis of biologically important phosphate analogues: exploring H-phosphonate and C-phosphonate chemistry
Stockholm University.
1999 (English)Doctoral thesis, comprehensive summary (Other academic)Alternative title
  :   (English)
Abstract [en]

This thesis is based on studies directed towards the development of methods for the preparation of phosphorus containing natural products, with the focus on C-phosphonate nucleic acid analogues.

Mechanistic studies concerning formation of the phosphorus-carbon bond resulted in development of two efficient protocols for the synthesis of C-phosphonates from the corresponding H-phosphonate derivatives. These were applied, inter alia, to the synthesis of a novel type of nucleotide analogue containing the 4-pyridylphosphonate internucleotide bond. Also, synthesis of new nucleoside 5'-methylenephosphonate building blocks, suitable for incorporation into oligonucleotides or their conjugates, and a new method for the preparation of alkyl H-phosphonates, are discussed. Finally, mechanistic investigations related to C-phosphonates formation via N->C phosphorus migration in certain complexes of DBU with chlorophosphates, are presented.

Place, publisher, year, edition, pages
Stockholm: Stockholm University , 1999. , 51 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
URN: urn:nbn:se:su:diva-64034ISBN: 91-7153-933-6OAI: diva2:454411
Public defence
1999-06-01, 10:00
Härtill 7 uppsatser Available from: 2011-11-07 Created: 2011-11-07 Last updated: 2011-11-07Bibliographically approved

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