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Synthetic Studies on the Preparation of Dinucleoside Phenyl-Phosphonates and Phenyl-Phosphonothioates via Palladium(0) Catalyzed Cross-Coupling
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
2005 (English)In: / [ed] Michal Hocek, 2005, 195-199 p.Conference paper, Published paper (Refereed)
Abstract [en]

Separate diastereomers of protected dithymidine (3'-5')-phenylphosphonates and dithymidine (3'-5')phenylphosphonothioate were obtained via a palladium(0) catalysed stereo-specific cross-coupling reaction of separate diastereomers of corresponding dinucleoside H-phosphonate and dinucleoside H-phosphonothioate with halobenzenes.

Place, publisher, year, edition, pages
2005. 195-199 p.
Series
Collection Symposium Series, 7
Keyword [en]
phenylphosphonate, phenylphosphonothioate
National Category
Other Basic Medicine
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-38772OAI: oai:DiVA.org:su-38772DiVA: diva2:315041
Conference
XIII Symposium on Chemistry of Nucleic Acid Components
Available from: 2010-04-28 Created: 2010-04-28 Last updated: 2010-04-28Bibliographically approved
In thesis
1. Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs
Open this publication in new window or tab >>Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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.

Publisher
40 p.
Keyword
Phosphonate, phosphonothioate, H-phosphonate
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-37514 (URN)978-91-7447-020-8 (ISBN)
Public defence
2010-05-21, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 3: Accepted. Available from: 2010-04-29 Created: 2010-03-08 Last updated: 2010-04-28Bibliographically approved

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