42867-68-5Relevant articles and documents
Synthesis of novel 2′,3′-Didehydro-2′,3′- dideoxyinosine phosphoramidate prodrugs and evaluation of their anticancer activity
Borek, Weronika,Lewandowska, Marta,Kleczewska, Natalia,Ruszkowski, Piotr,Kacprzak, Karol,Celewicz, Lech
, p. 507 - 518 (2014)
An efficient synthesis of 4-chlorophenyl N-alkyl phosphoramidates of 2 ′,3 ′-didehydro-2 ′,3 ′-dideoxyinosine employing 4-chlorophenyl phosphoroditetrazolide as a phosphorylating agent is reported. Improved method for the synthesis of 2 ′,3 ′-didehydro-2
Synthesis of 2′,3′-dideoxyinosine via radical deoxygenation
Torii, Takayoshi,Izawa, Kunisuke,Cho, Dae Hyan,Jang, Doo Ok
, p. 985 - 988 (2008/03/28)
A synthetic method for 2′,3′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5′-O-diprotected-2′, 3′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5′-O-positions were effective for the ddI synthesis. Copyright Taylor & Francis Group, LLC.
Nucleic Acid Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogues
Robins, Morris J.,Wilson, John, S.,Madej, Danuta,Low, Nicholas H.,Hansske, Fritz,Wnuk, Stanislaw F.
, p. 7902 - 7908 (2007/10/03)
Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (α-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents.Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time.Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino- 2-fluoropurine riboside.Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH(-)) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds.Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides.Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides.A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses.New 13C NMR data for several types of unsaturated-sugar nucleosides are tabulated.These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.