Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
This thesis focuses on chemical transformations of H-phosphonate and H-phosphonothioate and can be divided in two parts. The first part, is devoted to the development of the palladium-catalyzed P-C bond formation. Both mechanistic and synthetic studies of the transformations have been performed. The stereochemical aspects of palladium catalyzed arylation and benzylation of DNA analogs containing H-phosphonate and H-phosphonothioate have been studied.
In chapter 5 the condensation using Mitsunobu reaction of H-phosphonate function and nucleoside has been studied. Efficient protocols for the synthesis of nucleoside H-phosphonate monoester were developed.
The last chapter deals with development of silylation-mediated transesterfication of phenyl H-phosphonothioate as a thiophosphonylating agent. The methodology was used to prepare nucleoside H-phosphonothioate monomeric building blocks in good yields.
Place, publisher, year, edition, pages
2010. , 40 p.
Phosphonate, phosphonothioate, H-phosphonate
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-37514ISBN: 978-91-7447-020-8OAI: oai:DiVA.org:su-37514DiVA: diva2:302629
2010-05-21, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Markiewicz, Wojciech T., Professor
Stawinski, Jacek, Professor
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 3: Accepted.
List of papers