Synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside. 2001

S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
AminoScience Laboratories, Ajinomoto Co., Inc. 1-1, Suzuki-cho, Kawasaki-ku, Kawasaki, Kanagawa 210-8681, Japan.

A synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (1, FddA) via a 6-chloro-9-(3-deoxy-beta-D-erythro-pentofuranosyl)-9H-purine (9), which was readily obtained from inosine (5), is described. Fluorination at the C2'-beta position of the purine 3'-deoxynucleoside with diethylaminosulfur trifluoride was improved by the introduction of a 6-chloro group and proceeded in moderate yield. Purine 3'-deoxynucleoside derivatives were also subjected to nucleophilic reactions with triethylamine trihydrofluoride and gave the desired fluorinated nucleoside in good yield. The safety and yield of the fluorination process were greatly improved by the use of triethylamine trihydrofluoride. The influence of the sugar ring conformation and 6-chloro group on the rate of the nucleophilic reaction against elimination are also discussed.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D003839 Deoxyadenosines Adenosine molecules which can be substituted in any position, but are lacking one hydroxyl group in the ribose part of the molecule. Adenine Deoxyribonucleosides,Adenylyldeoxyribonucleosides,Deoxyadenosine Derivatives,Deoxyribonucleosides, Adenine,Derivatives, Deoxyadenosine
D016048 Dideoxyadenosine A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite. 2',3'-Dideoxyadenosine,ddA (Antiviral),2',3' Dideoxyadenosine
D019380 Anti-HIV Agents Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. AIDS Drug,AIDS Drugs,Anti-AIDS Agents,Anti-AIDS Drug,Anti-HIV Agent,Anti-HIV Drug,Anti-AIDS Drugs,Anti-HIV Drugs,Agent, Anti-HIV,Agents, Anti-AIDS,Agents, Anti-HIV,Anti AIDS Agents,Anti AIDS Drug,Anti AIDS Drugs,Anti HIV Agent,Anti HIV Agents,Anti HIV Drug,Anti HIV Drugs,Drug, AIDS,Drug, Anti-AIDS,Drug, Anti-HIV,Drugs, AIDS,Drugs, Anti-AIDS,Drugs, Anti-HIV

Related Publications

S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
April 1975, Journal of medicinal chemistry,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
October 1999, Nucleosides & nucleotides,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
January 2007, Nucleosides, nucleotides & nucleic acids,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
September 1995, Bioorganic & medicinal chemistry,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
October 1966, The Journal of organic chemistry,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
April 1995, Bioorganic & medicinal chemistry,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
December 1971, The Journal of organic chemistry,
S Takamatsu, and T Maruyama, and S Katayama, and N Hirose, and M Naito, and K Izawa
December 1988, Carbohydrate research,
Copied contents to your clipboard!