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Nucleoside 5′-C-phosphonates: reactivity of the α-hydroxyphosphonate moiety
- Source :
-
Tetrahedron . May2006, Vol. 62 Issue 20, p4917-4932. 16p. - Publication Year :
- 2006
-
Abstract
- Abstract: We found that various dialkyl phosphites, dialkyl trimethylsilyl phosphites, and tris-trimethylsilyl phosphite reacted smoothly with nucleoside 5′-aldehydes to afford epimeric nucleoside 5′-C-phosphonates in high yields. A number of these compounds in both the 2′-deoxyribo and ribo series were prepared. In the case of 2′-deoxythymidine-5′-aldehyde, a thorough study was made on the influence of the 3′-hydroxyl protecting group, type of phosphite, base, and solvent, on the yield and epimeric ratio of the resulting 5′-hydroxyphosphonates. Partial stereoselectivity in favour of either R or S epimers was observed. An attempt to transform the α-hydroxyl of the phosphonate moiety into a halo or azido moiety was not successful. Only intramolecular substitution reaction of the mesyloxy group for an alkoxy residue of the 2-hydroxyethyl ester took place in a low yield. [Copyright &y& Elsevier]
- Subjects :
- *NUCLEOSIDES
*PHOSPHONATES
*PHOSPHONIC acids
*CHEMICAL reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 62
- Issue :
- 20
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 20551157
- Full Text :
- https://doi.org/10.1016/j.tet.2006.03.008