Synthesis of 8-substituted analogues of 2 '-deoxy-2 '-fluoroadenosine

Authors
Maruyama, T Kozai, S Manabe, T Yazima, Y Satoh, Y Takaku, H
Citation
T. Maruyama et al., Synthesis of 8-substituted analogues of 2 '-deoxy-2 '-fluoroadenosine, NUCLEOS NUC, 18(11-12), 1999, pp. 2433-2442
Citations number
18
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES & NUCLEOTIDES
ISSN journal
07328311 → ACNP
Volume
18
Issue
11-12
Year of publication
1999
Pages
2433 - 2442
Database
ISI
SICI code
0732-8311(1999)18:11-12<2433:SO8AO2>2.0.ZU;2-C
Abstract
After 3',5'-di-O-protection of 8-bromoadenosine, the product was converted to the arabinoside, which was successively treated with diethylaminosulfur trifluoride (DAST) and acid to afford 8-bromo-2'-deoxy-2'-fluoroadenosine. However, the formation of an 8,2'-anhydro compound was noted by treatment o f the arabinoside with alkali. Finally, the 8-oxo analog was obtained from the 8-bromo congener.