Synthesis of ribonucleoside 3′,5′‐cyclic phosphorothioates using a modified hydroxybenzotriazole phosphotriester approach
- 1 January 1987
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 106 (11) , 577-580
- https://doi.org/10.1002/recl.19871061106
Abstract
Phosphorothioylation of 3′,5′‐dihydroxyl ribonucleosides with O‐(2‐chlorophenyl) O, O‐bis[6‐(trifluoromethyl)‐1‐benzotriazolyl] phosphorothioate, followed by addition of N‐methyl‐imidazole and removal of protecting groups, gives ribonucleosides 3′,5′‐cyclic phosphorothioates. The latter compounds could also be prepared by phosphorothioylation of 2′,3′,5′‐trihydroxyl ribonucleosides.Keywords
This publication has 13 references indexed in Scilit:
- The p-nitrophenylethyl (NPE) group: A versatile new blocking group for phosphate and aglycone protection in nucleosides and nucleotidesPublished by Elsevier ,2001
- Synthesis of nucleoside 3′,5′-cyclic phosphorothioatesTetrahedron Letters, 1986
- One-step protection of the nucleoside base in thymidine and uridineTetrahedron Letters, 1985
- NUCLEOSIDE PHOSPHOROTHIOATESAnnual Review of Biochemistry, 1985
- Use of 2,5-dichlorophenyl phosphorodichloridothioate in the synthesis of diastereoisomeric dinucleoside phosphorothioatesJournal of the Chemical Society, Chemical Communications, 1983
- A new approach to the synthesis of phosphotriester intermediates of nucleosides and nucleic acidsTetrahedron Letters, 1981
- Stereospecific synthesis of adenosine 3′,5′-(SP)- and -(RP)-cyclic phosphorothioates (cAMPS)Journal of the Chemical Society, Chemical Communications, 1979
- Adenosine 3',5'-cyclic phosphorothioate. Synthesis and biological propertiesBiochemistry, 1974
- Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1‐Hydroxy‐benzotriazolenEuropean Journal of Inorganic Chemistry, 1970
- The Synthesis of oligoribonucleotides—IVTetrahedron, 1968