Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-fluoroadenine.
A convenient synthesis of 2'-deoxy-2-fluoroadenosine from commercially available 2-fluoroadenine is described. The coupling reaction of silylated 2-fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside gave the corresponding 2-fluoro-2'-deoxyadenosine derivative (alpha/beta = 1:1) in good yield. The alpha- and beta-anomers were separated by chromatography, and then desilylated to give compounds 1a and 1b.
Ye
Song
S
Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA.
Rezende
Martha M
MM
Deng
Wei-Ping
WP
Kirk
Kenneth L
KL
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry*; D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
C412233:2'-deoxy-2-fluoroadenosine; D003839:Deoxyadenosines; C038208:2-fluoroadenine; D000225:Adenine