Synthesis of 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine.
The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N2, O3', O5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine (6c, GfpG).
Maruyama
Tokumi
T
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan. maruyama@ph.bunri-u.ac.jp
Kozai
Shigetada
S
Nakamura
Kazuo
K
Irie
Masachika
M
D015195:Drug Design; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
C476876:2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine; D006151:Guanosine