Chemical and Pharmaceutical Bulletin p. 966 - 970 (1999)
Update date:2022-07-30
Topics:
Maruyama, Tokumi
Takamatsu, Satoshi
Kozai, Shigetada
Satoh, Yoshiko
Izawa, Kunisuke
A facile and practical method to introduce fluorine at the up-side of the 2'-carbon of nucleosides is described. 6-Chloropurine riboside 3 was converted to the 3'-O-benzoate 4a via a stannylene complex, then converted to the 3'-O-benzoyl-5'-O-tritylriboside 5a. In the presence of pyridine, migration of the 3'-benzoyl groups of 4a and 5a to 2'-OH was rather slow. Hence, 5a was reacted with diethylaminosulfur trifluoride (DAST) in CH2Cl2 in the presence of pyridine to give the 2'-deoxy-2'-fluoroarabinoside 6 in good yield. The 3'-O-benzoyl-5'-O-trityl protecting system was easy to deprotect selectively. Thus, treatment of 6 with ammonia in MeOH gave the 5'- O-trityl compound 7, which was subjected to esterification with phenyl chlorothionoformate, radical deoxygenation with tris(trimethylsilyl)silane and acid treatment to afford 9-(2,3-dideoxy-2-fluoro-β-D-threo- pentofuranosyl)adenine (FddA) 2. In addition, acid treatment of 7 gave 9-(2- deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (FdaraA) 1.
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Doi:10.1016/j.bmcl.2006.08.018
(2006)Doi:10.1021/jo001755r
(2001)Doi:10.1021/jo00831a046
(1970)Doi:10.1007/s11095-006-9187-y
(2007)Doi:10.1021/jo00170a001
(1983)Doi:10.1002/(SICI)1099-0690(199906)1999:6<1489::AID-EJOC1489>3.0.CO;2-1
(1999)
