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
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.
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.
