244140-86-1Relevant articles and documents
Synthesis and in vitro antiviral activity evaluation of 9-(2-azido-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine derivatives
Takamatsu,Izawa,Maruyama,Katayama,Hirose,De Clercq
, p. 1053 - 1057 (2001)
9-(2-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine derivatives (1a-e) containing a lipophilic function at the N-6 position in the purine ring were prepared and evaluated for their antiviral activity. The compounds 1a-e turned out to be inactive as an
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.
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
