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Electrophile-promoted addition of hydroxymethylphosphonate to 4′,5′-didehydronucleosides: a way to novel isosteric analogues of 5′-nucleotides
- Source :
-
Tetrahedron . May2007, Vol. 63 Issue 21, p4516-4534. 19p. - Publication Year :
- 2007
-
Abstract
- Abstract: An electrophile-promoted addition of dialkyl-hydroxymethylphosphonate to the protected 4′,5′-didehydronucleosides resulted in an epimeric mixture of 4′-dialkylphosphonomethoxy derivatives of 2′,5′-dideoxynucleosides, novel analogues of 2′-deoxynucleoside 5′-monophosphates. Several types of electrophiles (pyridinium tosylate, NIS, NBS, MCPBA and others) were evaluated in addition reactions with 4′,5′-didehydrothymidine. Out of them, pyridinium tosylate was found to have a practical usefulness in these transformations. Its use has led to the preparation of a series of 4′-phosphonomethoxy derivatives of common 2′-deoxynucleosides. On biological screening, these free phosphonic acids exerted no significant cytostatic or antiviral activity. [Copyright &y& Elsevier]
- Subjects :
- *PHOSPHONATES
*PHOSPHONIC acids
*NUCLEIC acids
*CHEMICAL reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 63
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 24783985
- Full Text :
- https://doi.org/10.1016/j.tet.2007.03.059