- An effective and convenient synthesis of cordycepin from adenosine
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Cordycepin is a purine nucleoside analog with potent and diverse biological activities. Herein, we designed two methods to synthesize cordycepin. One method mainly converted the 3′-OH group into an iodide group and further dehalogenation to yield the final product. Although this method presented a short synthetic procedure, the synthesis had a low overall yield, resulting in only 13.5% overall yield. To improve the overall yield of cordycepin, another synthetic route was studied, which consisted of four individual steps: (1) 5′-OH protection (2) esterification (3) -O-tosyl (-OTs) group removal (4) deprotection. The key step in the synthetic method involved the conversion of 5′-O-triphenylmethyladenosine to 3′-O-tosyl-5′-O-triphenylmethyladenosine, using LiAlH4 as reducing agent. The main advantages of this route were an acceptable total product yield and the commercial availability of all starting materials. The optimal reaction conditions for each step of the route were identified. The overall yield of cordycepin obtained from adenosine as the starting material was 36%.
- Huang, Shen,Liu, Hui,Sun, Yanhua,Chen, Jian,Li, Xiufang,Xu, Jiangfeng,Hu, Yuwei,Li, Yuqing,Deng, Zhiwei,Zhong, Shian
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- Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
- Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
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p. 3910 - 3917
(2017/03/27)
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- An efficient and selective method for the preparation of triphenylmethyl ethers of alcohols and nucleosides
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A very simple and efficient method is described for the protection of alcohols and nucleosides with benzyl monomethoxytrityl and benzyl dimethoxytrityl ethers in the presence of diethylazodicarboxylate and a catalytic amount of ceric triflate. High selectivity was observed for the tritylation of 5'-OH function of nucleosides.
- Zekri, Negar,Alamdari, Reza Fareghi
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scheme or table
p. 563 - 568
(2010/08/05)
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- A solvent free and selective method for preparation of triphenylmethyl ethers of alcohols and nucleosides
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A very simple and efficient method is described for protection of alcohols and nucleosides with trityl(triphenylmethyl), mono and dimethoxytrityl chlorides in the presence of triethylamine under microwave irradiation. High selectivity was observed for tritylation of 5'-OH function of nucleosides.
- Zekri, Negar,Alamdari, Reza Fareghi,Khalafi-Nezhad, Ali
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experimental part
p. 299 - 304
(2012/04/23)
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- Design, synthesis and anti flaviviridae activity of N6-, 5′,3′-O- and 5′,2′-O-substituted adenine nucleoside analogs
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During a random screening of representative libraries of nucleoside analogues we discovered that the adenine derivatives FEVB28 and FEG118 were Flaviviridae inhibitors endowed with potency comparable, if not superior, to that of ribavirin. Those studies prompted us to design a new class of protected nucleoside analogs, reported herein, which displays interesting anti-bovine viral diarrhea virus (BVDV) activity and low cytotoxicity in cell-based assays (4, 23, 29 EC50: 14, 11, 26 μM respectively, CC50 > 100 μM) and appreciable activity in enzyme assays against the RNA dependent RNA polymerase (RdRp) of BVDV (4, 23, 29, RdRp inhibition activity 27, 16, 15 μM respectively). A molecular modeling study was also carried out to highlight the possible interactions between this compounds class and the corresponding hepatitis C virus (HCV) enzyme.
- Angusti, Angela,Manfredini, Stefano,Durini, Elisa,Ciliberti, Nunzia,Vertuani, Silvia,Solaroli, Nicola,Pricl, Sabrina,Ferrone, Marco,Fermeglia, Maurizio,Loddo, Roberta,Secci, Barbara,Visioli, Anna,Sanna, Tiziana,Collu, Gabriella,Pezzullo, Margherita,La Colla, Paolo
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experimental part
p. 423 - 432
(2009/04/11)
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