110143-10-7Relevant articles and documents
Convenient synthesis of fluorinated nucleosides with perfluoroalkanesulfonyl fluorides
Takamatsu, Satoshi,Katayama, Satoshi,Hirose, Naoko,De Cock, Etienne,Schelkens, Geert,Demillequand, Marc,Brepoels, Jozef,Izawa, Kunisuke
, p. 849 - 861 (2002)
Perfluoroalkanesulfonyl fluorides are effective dehydroxy-fluorination agents for the hydroxyl group at the sugar moiety of nucleoside derivatives and give the corresponding fluorinated nucleosides in good yield with an inversion of configuration in a sin
Practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) via a purine 3′-deoxynucleoside
Takamatsu, Satoshi,Maruyama, Tokumi,Katayama, Satoshi,Hirose, Naoko,Naito, Masaki,Izawa, Kunisuke
, p. 2325 - 2328 (2001)
A practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) via a 6-chloro-9-(3-deoxy-β-D-erythro-pentofuranosyl)-9H-purine (6) is described. Fluorination at the C2′-β position of the purine 3′-deoxynucleoside was improved
A stereoselective synthesis of 9-(3-O-benzyl-5-O-tetrahydropyranyl-β- D-arabinofuranosyl)adenine, a potentially useful intermediate for ribonucleoside synthesis
Woltermann, Christopher J.,Lapin, Yuri A.,Kunnen, Kevin B.,Tueting, David R.,Sanchez, Ignacio H.
, p. 3445 - 3449 (2007/10/03)
A novel synthesis for preparing 9-(3-O-benzyl-5-O-tetrahydropyranyl-β- D-arabinofuranosyl)adenine (6) has been developed which does not require sub zero temperatures or exotic reagents. A key step in this synthesis is the selective protection of the 3′-OH of ara-A with a benzyl group. The 5′-OH is then selectively protected with DHP to yield 6, a potentially useful intermediate. A synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo- pentofuranosyl)adenine (1, FddA), an anti-viral compound, is given to illustrate the utility of this new approach.
An industrial process for synthesizing lodenosine (FddA)
Izawa, Kunisuke,Takamatsu, Satoshi,Katayama, Satoshi,Hirose, Naoko,Kozai, Shigetaka,Maruyama, Tokumi
, p. 507 - 517 (2007/10/03)
Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3′-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.
A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone
Choudhury, Anusuya,Jin, Fuqiang,Wang, Dengjin,Wang, Zhe,Xu, Guoyou,Nguyen, Dieu,Castoro, John,Pierce, Michael E.,Confalone, Pat N.
, p. 247 - 250 (2007/10/03)
Anti-HIV agent β-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly syn-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation.
Improved synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) using triethylamine trihydrofluoride
Takamatsu, Satoshi,Maruyama, Tokumi,Katayama, Satoshi,Hirose, Naoko,Izawa, Kunisuke
, p. 2321 - 2324 (2007/10/03)
An improved synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) via a fluorination of 3′-O-benzoyl-5′-O-tritylriboside (4a) using noncorrosive triethylamine trihydrofluoride (Et3N·3HF) is described. The method is suitable for large-scale synthesis. In particular, the synthesis of the pivotal intermediate 4a was much improved in avoidance of the use of toxic tin reagent. Radical deoxygenation with several silanes was also studied. The total yield of FddA from 6-chloropurine riboside (2) in this study was greater than that we reported previously.
Synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA) via a purine 3′-deoxynucleoside
Takamatsu,Maruyama,Katayama,Hirose,Naito,Izawa
, p. 7469 - 7477 (2007/10/03)
A synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) via a 6-chloro 9-(3-deoxy-β-D-erythro-pentofuranosyl)-9H-purine (9), which was readily obtained from inosine (5), is described. Fluorination at the C2′-β 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.
(2R,3S,5S)-2-Acetoxy-3-fluoro-5-(p-toluoyloxymethyl)tetrahydrofuran: A key intermediate for the practical synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA)
Jin, Fuqiang,Wang, Dengjin,Confalone, Pat N.,Pierce, Michael E.,Wang, Zhe,Xu, Guoyou,Choudhury, Anusuya,Nguyen, Dieu
, p. 4787 - 4789 (2007/10/03)
A highly efficient synthesis of (2R,3S,5S)-2-acetoxy-3-fluoro-5-(p-toluoyloxymethyl)tetrahydrofuran (2a) was developed. As a key intermediate, 2a was effectively applied to the synthesis of 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (FddA), thus, providing a practical synthetic approach to FddA.
α-D-pentofuranosides, and a process for preparing the same
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, (2008/06/13)
α-D-pentofuranoside derivatives have the general formula (D), in which R stands for (C1-C4)alkyl that is non-substituted or substituted one or several times by halogen, (C1-C4)alkyl, (C1-C4
Methods for producing nucleoside derivatives and intermediates therefor
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, (2008/06/13)
Novel intermediates of nucleoside derivatives, of which the 6-position of the nucleic acid base moiety is substituted with a halogen atom, are produced. Using those novel intermediates, even substrates, of which the 3'-position of the saccharide moiety is
