Introduction of a benzoyl group onto 6-chloropurine riboside in aqueous solution and its application to the synthesis of nucleoside derivatives.
A benzoyl group was introduced onto the 3'-hydroxyl group of 6-chloropurine riboside by treatment with benzoic anhydride in the presence of a base in aqueous solution. The product (3b) was converted to 9-(2,3-Di-deoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (1, FddA) in 6 steps, including radical deoxygenation.
Maruyama
T
T
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
Kozai
S
S
Takamatsu
S
S
Izawa
K
K
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates; D016048:Dideoxyadenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008722:Methods; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D012996:Solutions; D014867:Water
D019380:Anti-HIV Agents; D001565:Benzoates; D011684:Purine Nucleosides; D012996:Solutions; D014867:Water; C055502:2-fluoro-2',3'-dideoxyadenosine; C024008:6-chloropurine riboside; D016048:Dideoxyadenosine; C102988:benzoic anhydride