Carbocyclic Analogues of 3′,4′-Didehydro-2′-deoxyribofuranosyl-2,4(1H,3H)-pyrimidinediones
- 1 September 1994
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 13 (9) , 1929-1937
- https://doi.org/10.1080/15257779408010673
Abstract
A new method for obtaining carbocyclic analogues of 3′,4′-didehydro-2,4(1H,3H)-pyrimidinedione nucleosides in good yields consists of the reaction of the carbocyclic 2,3′-anhydronucleosides with lithium chloride in dimethylformamide. Small amounts of the carbocyclic 2′,3′-didehydro isomers are formed simultaneously. The carbocyclic 2,3′-anhydronucleosides were obtained by treating carbocyclic 5′-trityl derivatives with DAST.Keywords
This publication has 17 references indexed in Scilit:
- Synthesis of chiral carbocyclic nucleosidesTetrahedron, 1992
- Stereospecific synthesis and antiviral properties of different enantiomerically pure carbocyclic 2'-deoxyribonucleoside analogs derived from common chiral pools: (+)-(1R,5S)- and (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-oneJournal of Medicinal Chemistry, 1990
- Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosidesJournal of Medicinal Chemistry, 1990
- Synthetic studies towards (−)-carba-3′-deoxy-3′-fluorothymidine.Tetrahedron, 1989
- Total synthesis of (-)-neplanocin AThe Journal of Organic Chemistry, 1988
- Potent and selective activity of a new carbocyclic nucleoside analog (Carbovir: NSC 614846) against human immunodeficiency virus In vitroBiochemical and Biophysical Research Communications, 1988
- Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral propertiesJournal of Medicinal Chemistry, 1988
- Enantioselective synthesis of new analogs of neplanocin A and their biological activityCarbohydrate Research, 1987
- Carbocyclic nucleosidesMedicinal Research Reviews, 1986
- Synthesis of the carbocyclic analogue of the antiviral nucleoside (E)-5-(2-bromovinyl)-2′-deoxyuridineJournal of the Chemical Society, Perkin Transactions 1, 1986