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Synthetic studies on the preparation of nucleoside 5'-H-phosphonate monoesters under the Mitsunobu reaction conditions
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2009 (English)In: ARKIVOC, ISSN 1424-6376, no 3, 20-27 p.Article in journal (Refereed) Published
Abstract [en]

A reaction of suitably protected nucleosides with phosphonic acid in the presence of diethyl azodicarboxylate and triphenylphosphine in pyridine provided in good yields the corresponding 5’-H-phosphonate monoesters.

Place, publisher, year, edition, pages
2009. no 3, 20-27 p.
Keyword [en]
H-Phosphonate monoesters, phosphonic acid, the Mitsunobu reaction
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-30074ISI: 000265191400004OAI: oai:DiVA.org:su-30074DiVA: diva2:241178
Note

Dedicated to Professor Harri Lönnberg on the occasion of his 60th birthday (in part III)

Title according to journal's index: Synthetic studies on nucleoside 5'-H-phosphonate monoesters under Mitsunobu reaction conditions

Available from: 2009-10-01 Created: 2009-10-01 Last updated: 2017-12-13Bibliographically 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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