Synthesis of 2′,3′-Dideoxyuridine Via the Corey-Winter Reaction
- 1 January 1989
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 8 (1) , 35-41
- https://doi.org/10.1080/07328318908054156
Abstract
Heating of 5′-protected uridine cyclic 2′,3′-O-thiocarbonates in trimethyl phosphite in an inert atmosphere gives 5′-protected 2′,3′-didehydro-2′,3′-dideoxy-uridines in nearly quantitative yield.This publication has 15 references indexed in Scilit:
- 3'-Substituted 2',3'-dideoxynucleoside analogs as potential anti-HIV (HTLV-III/LAV) agentsJournal of Medicinal Chemistry, 1987
- Antiviral activity of 2′,3′-dideoxycytidin-2′-ene (2′,3′-dideoxy-2′,3′-didehydrocytidine) against human immunodeficiency virus in vitroBiochemical Pharmacology, 1987
- Both 2′,3′-dideoxythymidine and its 2′,3′-unsaturated derivative (2′,3′-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitroBiochemical and Biophysical Research Communications, 1987
- Partial protection of carbohydrate derivatives. part 18. simple, preparative procedure for 5'--acylribonucleosides; highly regioselective -deacylation at 2' and 3' positions of fully acylated purine and pyrimidine ribonucleoside through sodium methoxide-thf systemTetrahedron, 1985
- A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2′-ene and 2t',3′-dideoxynucleosidesTetrahedron Letters, 1984
- Reactions of 2-Acyloxyisobutyryl Halides with Nucleosides. 1V.l A Facile Synthesis of 2,3-Unsaturated Nucleosides Using Chromous AcetateThe Journal of Organic Chemistry, 1974
- Purine Nucleosides. XIV. Unsaturated Furanosyl Adenine Nucleosides Prepared via Base-Catalyzed Elimination Reactions of 2'-Deoxyadenosine Derivatives1Journal of the American Chemical Society, 1966
- Nucleosides. IX. The Formation of 2',3'-Unsaturated Pyrimidine Nucleosides via a Novel β-Elimination Reaction1,2The Journal of Organic Chemistry, 1966
- Nucleosides. II. Reactions of 5'-Trityluridine 2',3'-O-ThionocarbonateThe Journal of Organic Chemistry, 1965
- A New, Stereospecific Olefin Synthesis from 1,2-DiolsJournal of the American Chemical Society, 1963