Synthesis of 2‘,3‘-Didehydro-2‘,3‘-dideoxynucleosides by Reaction of 5‘-Protected Nucleoside 2‘,3‘-Dimesylates with Telluride Dianion: A General Route from Cis Vicinal Diols to Olefins
The Journal of Organic Chemistry1996Vol. 61(21), pp. 7426–7437
Citations Over TimeTop 10% of 1996 papers
Abstract
2',3'-Dimesylates of 5'-protected nucleosides are converted into the corresponding 2',3'-didehydro-2',3'-dideoxy compounds by treatment with telluride dianion in the form of the sodium or lithium salt. The method is well-suited to the preparation of unsaturated nucleosides that can be converted into compounds that are believed to be useful in the treatment of AIDS. The deoxygenation is general for vicinal dimesylates that have, or may adopt, a synperiplanar conformation. With straight chain compounds the reaction is stereospecific. In some cases, similar, but slower, deoxygenations can be performed with selenide dianion.
Related Papers
- → The role of nucleoside transporters in cancer chemotherapy with nucleoside drugs(2007)230 cited
- → Nucleoside transport and its significance for anticancer drug resistance(1998)153 cited
- → Transport and mode of action of nucleoside derivatives used in chemical and antiviral therapies(1998)117 cited
- → Identification of Structural and Molecular Features Involved in the Transport of 3′-Deoxy-Nucleoside Analogs by Human Equilibrative Nucleoside Transporter 3(2018)9 cited
- → The Role of Nucleoside Transport in the Antineoplastic Activity of Purine Nucleoside Chemotherapeutic Agents(2008)2 cited