31085-52-6Relevant academic research and scientific papers
Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside
Faul, Margaret M.,Huff, Bret E.,Dunlap, Steven E.,Frank, Scott A.,Fritz, James E.,Kaldor, Stephen W.,LeTourneau, Michael E.,Staszak, Michael A.,Ward, Jeffrey A.,Werner, John A.,Winneroski, Leonard L.
, p. 8085 - 8104 (2007/10/03)
The synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine 1 was accomplished using two different approaches. First, uridine and cytidine were used to prepare the key intermediate epoxides 15 and 31 which were opened with cyanide, deoxygenated by elimination to vinyl nitriles 17 and 36, and reduced by 1,4 hydride addition to the saturated nitriles 18 and 37. Secondly, a novel Rh-catalyzed hydroformylation reaction of 2',3'-didehydro-2',3'-dideoxycytidine 46 was used to prepare 1 in four steps. The attempted use of 2'-deoxyuridine and 2'-deoxycytidine to prepare 1 is also discussed.
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
Clive, Derrick L. J.,Wickens, Philip L.,Sgarbi, Paulo W. M.
, p. 7426 - 7437 (2007/10/03)
2′,3′-Dimesylates of 5′-protected nucleosides are converted into the corresponding 2′,3′-didehydro2′,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.
